4-Fluorophenol → Tert-butyl 2-(4-fluorophenoxy)acetate

Participants

Reaction Steps

tert-Butyl-2-bromoacetate (1.95 g, 10.0 mmol) was added to a mixture of 4-fluorophenol (1.12 g, 10.0 mmol) and NaOH (400 mg, 10.0 mmol) in N,N-dimethylformamide (15 ml) and stirred at room temperature for 17 hours. The reaction was quenched with H2O (50 ml) and extracted by ethyl acetate (50 ml×3). The combined organic phase was washed with H2O (50 ml×4) and brine (50 ml), dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl 2-(4-fluorophenoxy)acetate (2.16 g, 95%) as yellow oil: LC-MS: 171 [M−55]+.

Provenance & Evidence