2-bromo-1-phenylethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromoacetophenone (1 g) was dissolved in tetrahydrofuran (8 ml), and a solution of borane-dimethylamine (326 mg) in tetrahydrofuran (6 ml) was added thereto at room temperature. After the reaction mixture was stirred at room temperature for 60 hours, methanol (1 ml) and 1 M hydrochloric acid aqueous solution (5 ml) were added thereto, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After removing the solvent by distillation from the organic layer, the residue was purified by silica gel column chromatography to obtain the title compound from a fraction eluted with hexane-ethyl acetate (5:1). at room temperature the mixture was extracted with diethyl ether The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate After removing the solvent by distillation from the organic layer the residue was purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 21.9 g of 5-(2-aminoethoxy)-salicylamide, 36.0 g of α-(bromomethyl)-benzyl alcohol and 30 g of potassium bicarbonate in 240 ml of ethanol is refluxed for 15 hours, with stirring. The reaction mixture is then cooled and filtered and the filtrate is evaporated. The evaporation residue is partitioned between 300 ml of ethyl acetate and 100 ml of water and the organic phase is separated off, dried over magnesium sulfate and evaporated. The residue is dissolved hot in as little ethanol as possible and made to crystallise, yielding α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)ethyl]-aminomethyl]-benzyl alcohol with a melting point of 174°-175° (from ethanol). is refluxed for 15 hours The reaction mixture is then cooled filtered the filtrate is evaporated The evaporation residue is partitioned between 300 ml of ethyl acetate and 100 ml of water the organic phase is separated off dried over magnesium sulfate evaporated The residue is dissolved hot in as little ethanol as possible and to crystallise