Bromoacetyl Bromide: A Versatile and Selective Cleaving Agent for Ethers and Acetals

Viljoen, Murray S.

doi:10.1081/scc-120002510

Cited by 9 publications

(4 citation statements)

References 12 publications

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“…Compound 3r was synthesized following the general procedure starting from 2,6-dimethylphenylboronic acid (150 mg, 1.00 mmol) and 4-bromobutyl bromoacetate (411 mg, 1.50 mmol). After column chromatography (SiO 2 , hexane/ethyl acetate 5:1), 3r was isolated as a colorless liquid (144 mg, 48%).…”

Section: Methodsmentioning

confidence: 99%

“…Compound 3h was prepared according to the general protocol starting from 4-chloro-2,6-dimethylphenylboronic acid (186 mg, 1.00 mmol) and ethyl bromoacetate (167 mg, 1.50 mmol). After column chromatography (SiO 2 , hexane/ethyl acetate 5:1), 3f was isolated as a colorless oil that crystallized upon cooling; 1 H NMR (400 MHz, CDCl 3 ) δ 7.02 (s, 2H), 4.13 (q, J = 7.2 Hz, 2H), 3.62 (s, 2H), 2.29 (s, 6H), 1.23 (t, J = 7.2 Hz, 3H) ppm; 13 C NMR (101 MHz, CDCl 3 ) δ 170. 7, 139.0, 132.3, 130.3, 127.9, 60.8, 35.0, 20.1, 14. Table 2.…”

Section: Notementioning

confidence: 99%

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Palladium-Catalyzed Cross-Coupling of Sterically Demanding Boronic Acids with α-Bromocarbonyl Compounds

et al. 2011

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A catalyst system generated in situ from Pd(dba)(2) and tri(o-tolyl)phosphine mediates the coupling of arylboronic acids with alkyl α-bromoacetates under formation of arylacetic acid esters at unprecedented low loadings. The new protocol, which involves potassium fluoride as the base and catalytic amounts of benzyltriethylammonium bromide as a phase transfer catalyst, is uniquely effective for the synthesis of sterically demanding arylacetic acid derivatives.

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Section: Methodsmentioning

confidence: 99%

Section: Notementioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling of Sterically Demanding Boronic Acids with α-Bromocarbonyl Compounds

et al. 2011

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“…14a THF proved also not to be appropriate due to a side reaction with 3. 15 Among other solvents investigated as CH 3 CN, DMSO, tBuOH and DMF, tBuOH and DMF showed an overall homogeneous reaction with moderate to high yields (Table 1, entry 2-4). The use of tBuOH as solvent afforded a yield of 81% in the batch mode within 20 h at room temperature, whereas in the microreactor with 34 min residence time at 25°C only 50% yield of 4 was obtained.…”

Section: 9amentioning

confidence: 99%

Continuous-flow microreactor multi-step synthesis of an aminonaphthalene derivative as starting material for the preparation of novel anticancer agents

Tietze¹,

Li²

2008

Arkivoc

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A multi-step synthesis of the aminonaphthalene derivate 1 as a key intermediate in the synthesis of the duocarmycin based prodrug 2 for a selective treatment of cancer in a microreactor is described. The conditions for the synthesis in the batch mode were adjusted for application in a microreactor and the results of both methods were compared showing that the transformations in the microreactor in most cases give similar or even better results with the advantage of a continuous-flow production, higher safety and faster reactions with an empirical accelerating factor of F = 3-10.

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“…cefotetan and labetalol 1 and is also utilized for the selective cleavage of ethers and acetals and exploited for the selective extension of carbon chains. 2 Spectroscopic investigations have shown that bromoacetyl bromide in both gaseous and liquid phases is a mixture of two conformers, anti and gauche in the ratio of 40:60, respectively. 3 Bromoacetyl bromide is prepared by reaction of acetic acid and bromine in the presence of red phosphorous at 140°C.…”

Section: Introductionmentioning

confidence: 99%