Hydrochloric Acid Catalysis of N-Bromosuccinimide (NBS) Mediated Nuclear Aromatic Brominations in Acetone

Andersh, Brad; Murphy, Drew; Olson, Ryan J.

doi:10.1080/00397910008087387

Cited by 35 publications

(13 citation statements)

References 21 publications

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“…(2,6‐Dimethylphenyl)boronic acid was filtered through a pad of silica ( n ‐hexane/Et 2 O, 2:1 v/v) prior to use. Rac ‐ 4 ,35 ( S p )‐ 4 ,36 [Pd(cod)Cl 2 ],37 2‐bromo‐1,3,5‐triphenylbenzene,38 2‐bromo‐1,3‐dimethoxybenzene,39 1‐bromo‐2‐methoxynaphthalene,40 1‐bromo‐2‐methylnaphthalene,41 1‐bromo‐2‐phenylnaphthalene,42 9‐bromoanthracene,43 2‐bromo‐3,5‐dimethylbenzaldehyde,44 (2‐methoxyphenyl)boronic acid,45 (2‐isopropylphenyl)boronic acid,46 mesitylboronic acid,47 (2‐methylnaphthalen‐1‐yl)boronic acid,48 and (2,6‐dimethoxyphenyl)boronic acid49 were synthesized according to previously published procedures.…”

Section: Methodsmentioning

confidence: 99%

A Planar‐Chiral Phosphino(alkenyl)ferrocene for Suzuki–Miyaura C–C Coupling Reactions

et al. 2014

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A simple method for the functionalization of closo‐borates [closo‐B10H10]2− (1), [closo‐1‐CB9H10]− (2), [closo‐B12H12]2− (3), [closo‐1‐CB11H12]− (4), and [3,3′‐Co(1,2‐C2B9H11)2]− (5) is described. Treatment of the anions and their derivatives with ArI(OAc)2 gave aryliodonium zwitterions, which were sufficiently stable for chromatographic purification. The reactions of these zwitterions with nucleophiles provided facile access to pyridinium, sulfonium, thiol, carbonitrile, acetoxy, and amino derivatives. The synthetic results are augmented by mechanistic considerations.

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Section: Methodsmentioning

confidence: 99%

A Planar‐Chiral Phosphino(alkenyl)ferrocene for Suzuki–Miyaura C–C Coupling Reactions

et al. 2014

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“…The first step was methyl ether protection of phenolic –OH by reaction of 3‐pentadecyl phenol with methyl iodide using potassium hydroxide as the base and dimethyl sulfoxide as the solvent . 3‐Pentadecyl anisole was brominated using N ‐bromosuccinimide and a catalytic amount of HCl in acetone as a solvent to obtain 4‐bromo‐3‐pentadecyl anisole . 4‐Bromo‐3‐pentadecyl anisole on Suzuki coupling reaction with 4‐methoxyphenylboronic acid in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium and potassium carbonate in toluene as a solvent afforded 4,4′‐dimethoxy‐2‐pentadecyl‐1,1′‐biphenyl .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

Tawade

Shaligram

Valsange

et al. 2016

Polymer International

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A new biphenol, 3-pentadecyl 4,4 ′ -biphenol, was synthesized starting from 3-pentadecylphenol and was polycondensed with 4,4 ′ -difluorobenzophenone, 1,3-bis(4-fluorobenzoyl)benzene and bis(4-fluorophenyl)sulfone to obtain poly(arylene ether)s with biphenylene linkages in the backbone and pendent pentadecyl chains. Inherent viscosities and number-average molecular weights (M n ) of the poly(arylene ether)s were in the range 0.50 − 0.81 dL g −1 and 2.2 × 10 4 − 8.3 × 10 4 , respectively. Detailed NMR spectroscopic studies of the poly(arylene ether)s indicated the presence of constitutional isomerism which existed because of the non-symmetrical structure of 3-pentadecyl 4,4 ′ -biphenol. The poly(arylene ether)s readily dissolved in common organic solvents such as dichloromethane, chloroform and tetrahydrofuran and could be cast into tough, transparent and flexible films from their chloroform solutions. The poly(arylene ether)s exhibited T g values in the range 35-60 ∘ C which are lower than that of reference poly(arylene ether)s without pentadecyl chains. The 10% decomposition temperatures (T 10 ) of the poly(arylene ether)s were in the range 410-455 ∘ C indicating their good thermal stability. A gas permeation study of poly(ether sulfone) containing pendent pentadecyl chains revealed a moderate increase in permeability for helium, hydrogen and oxygen. However, there was a large increase in permeability for carbon dioxide which could be attributed to the internal plasticization effect of pendent pentadecyl chains.

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“…[32] 3-Pentadecyl anisole was selectively brominated at para position to -OCH 3 using Nbromosuccinimide and catalytic amount of HCl in acetone as a solvent to give 4-bromo 3-pentadecyl anisole. [35] Further, 4-bromo 3-pentadecyl anisole was reacted with 4-methoxy phenol in the presence of potassium hydroxide and Cu as a catalyst under classical Ullmann etherification reaction conditions to form 4-methoxy-1-(4-methoxyphenoxy)-2-pentadecylbenzene, which on demethylation by standard procedure [36] in the presence of HBr and tetra n-butyl phosphonium bromide as a phase transfer catalyst afforded HPPDP. HPPDP and intermediates involved in its synthesis were characterized by IR and NMR spectroscopy.…”

Section: Synthesis Of 4-(4-hydroxyphenoxy)-3-pentadecylphenolmentioning

confidence: 99%

Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

et al. 2014

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A new bisphenol viz., 4-(4-hydroxyphenoxy)-3-pentadecylphenol (HPPDP) was synthesized starting from cashew nut shell liquid (CNSL). Aromatic (co)polyesters containing ether linkages in the main chain and pendent pentadecyl chains were synthesized by the interfacial polycondensation of HPPDP with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol %) and by polycondenation of varying composition of HPPDP and bisphenol-A (BPA) with TPC. The resultant (co)polyesters exhibited inherent viscosities in the range 0.70-1.21 dL g −1 and number-average molecular weights in the range 16,000-48,200 (GPC, polystyrene standard). Polyesters were soluble in common organic solvents such as chloroform and dichloromethane and could be cast into films from chloroform solution. Polyesters exhibited T 10 values in the range 430-455°C and Tg values were in the range 29-202°C. Dynamic mechanical storage modulus and maximum on transition of tan δ curve decreased with increased content of HPPDP in copolyesters. Importantly, the large difference between Tg and T 10 values offers the possibility to process these polyesters in the melt.

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Hydrochloric Acid Catalysis of N-Bromosuccinimide (NBS) Mediated Nuclear Aromatic Brominations in Acetone

Cited by 35 publications

References 21 publications

A Planar‐Chiral Phosphino(alkenyl)ferrocene for Suzuki–Miyaura C–C Coupling Reactions

A Planar‐Chiral Phosphino(alkenyl)ferrocene for Suzuki–Miyaura C–C Coupling Reactions

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

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