Hydrogen Peroxide → 2-Ethoxy-5-fluorophenol

Participants

Reaction Conditions

Reaction Steps

The 2-bromo-1-ethoxy-4-fluoro-benzene (3.1 g) described in example 1.1 was dissolved in THF (25 ml). The solution was cooled to −75° C. and a solution of n-BuLi (9.73 ml, 1.6 M in hexane) was added slowly. The mixture was stirred for 30 min at −75° C. Trimethylborate (1.62 g) was added within 5 min. Acetic acid (1.27 g) and a 30% solution of H2O2 (1.51 g) were added sequentially. The mixture was stirred for 30 min at 0° C. and for 3 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography (n-hexane/ethyl acetate) to yield 1.77 g of 2-ethoxy-5-fluoro-phenol as a colorless oil. MS: 156 ([M]+).

Provenance & Evidence