Hydrogen Bromide → 4-(2-Bromoethyl)phenol

Participants

Reaction Conditions

Reaction Steps

500 g 2-(4-hydroxyphenyl) ethanol was placed in a 5 L round bottom flask, to which 2960 g of 48% aq. HBr was added with stirring. The reaction mixture was placed in a bath at 75° C. After 2.5 h agitation 5 g of A11 seed crystals was added. The reaction mixture was stirred at this temperature for another 24 h. The reaction mixture was slowly cooled to 20° C. The precipitate was isolated by filtration and washed with 10% aq. sodium bicarbonate solution to give 700 g (96% yield) of the title product. 1H NMR (CDCl3); δ 3.10 (2H, t, J=7.8 Hz), 3.53 (2H, t, J=7.5 Hz), 6.80 (2H, d, J=8.4 Hz), 7.09 (2H, d, J=8.4 Hz).

Provenance & Evidence