Methanol → ((4-Bromobenzyl)oxy)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a flask containing NaH (1 g, 25 mmol) in dry THF (25 mL) at 0° C., was added a solution of 4-bromobenzyl alcohol (2.11 g, 11.3 mmol) in dry THF (10 mL). The solution was stirred at 0° C. for 1 h, then a solution of bromoacetic acid (1 g, 7.14 mmol) in dry THF (10 mL) was added. The solution was refluxed for 3 h, then cooled. A solution of MeOH (1 mL) in water (100 mL) was added, and mixture was extracted with EtOAc (2×20 mL). The water layer was acidified by 1N HCl to pH=2, then extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated to give 67A. (1.66 g, 95%). MS (ESI) m/z 169.0 (M-OCH2CO2 H)+.

Provenance & Evidence