A study on the metalation of alkoxydibromobenzenes

Long‐Range Effects in the Metalation/Boronation of Functionalized 1,4‐Dihalobenzenes

“…(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) zene may be problematic due to a formation of other kinetically favoured products. [10] This result has prompted us to evaluate more precisely the influence of steric and electronic factors on the regioselectivity of the metalation of 2-functionalized 1,4-dihalobenzenes with special emphasis on the role of long-range inductive effects.…”

Selective recovery of a pyridine derivative from an aqueous waste stream containing acetic acid and succinonitrile with solvent impregnated resins

“…The solid was dried in vacuo and stripped with toluene yielding a pale yellow solid (73 g, 0.248 mol, 99%). C NMR data identical to [33]. A similar reaction has been performed on 0.1 mol scale.…”

“…4, and starts from 3,5-dibromophenol 3 which was protected by a bulky trimethylsilyl group. The para-position of compound 4 was selectively deprotonated by lithium diisopropylamine (LDA) as reported previously [33], and the anion quenched with dimethylformamide (DMF) to afford aldehyde 5. After initial unsuccessful attempts to keep the TMS protected group intact by quenching the reaction with base, pure 2,6-dibromo-4-hydroxybenzaldehyde 5 was isolated after quenching with acid.…”

“…Appendix A 2,6-Dibromo-4-hydroxybenzaldehyde (5) was prepared in two steps from 3,5 dibromophenol 3 according to a procedure as described by Dabrowski [33]. 1-Bromo-3,5,5-trimethylhexane 11 [34] and 1-Bromo-3,7-dimethyloctane 12 [35] were prepared according to literature procedures.…”

Total Synthesis of Dictyodendrin A and B

“…After conversion of para-nitrophenol (8) into 2,6-dibromo-iodobenzene derivative 9 [5] in six steps, [6a] halogen-lithium exchange on treatment with BuLi in toluene at À78 8C, [6] followed by addition to nitroolefin 11 gave Michael adduct 12 in excellent yield.…”