Bromoacetic Acid → 2-(4-Bromo-2,6-dimethylphenoxy)acetic acid

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Reaction Steps

To a suspension of sodium hydride (60%, 437 mg, 10.9 mmol) in THF (10 mL) at rt, was added a solution of 4-bromo-2,6-dimethylphenol (1.00 g, 4.97 mmol) in THF (10 mL), over 5 min. The reddish suspension was stirred at rt for 10 min, then a solution of bromoacetic acid (691 mg, 4.97 mmol) in 5 mL THF was added. The suspension was stirred at rt for 20 h. The volatile solvent was evaporated in vacuo, then the mixture was diluted with 20 mL H2O. The pH was adjusted to 7 with 1N HCl, then the aqueous phase was extracted with Et2O (2×). The aqueous phase was acidified to pH=2 with 1N HCl, then was extracted with EtOAc (2×). The combined organic extract washed with brine, dried (Na2SO4) and concentrated to afford 1.10 g (85%) of 79A as a colorless solid. MS (ESI) m/z 259.0 (M+H)+.

Provenance & Evidence