4-Bromophthalic acid → (5-Bromo-2-(hydroxymethyl)phenyl)methanol

Participants

Reaction Steps

To a solution of 4-bromophthalic acid (3.0 g, 12.24 mmol) in 30 mL of THF was added a solution of borane-THF complex (1.0M) dropwise at 0° C. The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCl (2N) at 0° C. The product was extracted with ethyl acetate and washed with sat. NaCl, dried over Na2SO4, and concentrated under reduced pressure to afford 2.8 g (100%) of 4-bromo-2-hydroxymethylbenzyl alcohol as a colorless oil. 1H NMR (CDCl3) 7.28 (m, 2H), 7.26 (m, 1H), 4.69 (s, 4H), 2.80 (bs, 2H).

Provenance & Evidence