Ethyl Acetate → 3-(2-Bromobenzyl)-methoxy benzene

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (0.154 g, 4.06 mmol) was suspended in anhydrous Et2O (10 mL) under a N2 atmosphere and cooled (0° C.) with stirring. Anhydrous AlCl3 (1.08 g, 8.14 mmol)was dissolved in ice-cold anhydrous Et2O (20 mL) and added dropwise to the LiAlH4 suspension. After complete addition the suspension was stirred at the same temperature (20 min.). (2-Bromo-phenyl)-(3-methoxy-phenyl)-methanol [13] (0.68 g, 2.32 mmol) was dissolved in anhydrous Et2O (10 mL) and added dropwise via syringe to the suspension. After complete addition the reaction mixture was heated at reflux (4 h), cooled (0° C.) and EtOAc was added dropwise to destroy the excess of the reagent and the mixture was added to 20% aq. H2SO4 (50 mL). Et2O (50 mL) was added and extracted. The Et2O layer was separated, washed with water, brine, dried (MgSO4) and evaporated to give a reddish yellow oil. The oil was purified by mplc using pet. ether-CH2Cl2 (9:1) as eluent to give 0.485 g (75%) of the pure product as a colorless oil. 1H NMR (CDCl3)d: 3.81 (s, 3H, CH3), 4.14 (s, 2H, CH2), 6.79-7.62 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 42.34, 55.69, 112.07, 122.02, 125.48, 128.07, 128.50, 130.02, 131.66, 133.43.

Provenance & Evidence