2-Bromophenol → HCID 69417921, compound

Participants

Reaction Conditions

Reaction Steps

A first intermediate compound 3-(2-Bromo-phenoxy)-2,2-dimethyl-propionic acid, was produced as follows: To a mixture of 3-methanesulfonyloxy-2,2-dimethyl-propionic acid methyl ester (20.00 g, 95.23 mmol) and 2-bromophenol (16.48 g, 95.23 mmol) in acetonitrile (200 mL) was added Cs2CO3 (46.50 g, 142.80 mmol) and the mixture was heated at 100° C. in a sealed flask overnight. The resulting suspension was filtered. The solvent was evaporated and the crude material was partitioned between dichloromethane (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL), dried over Na2SO4 and evaporation of the solvent gave 3-(2-bromo-phenoxy)-2,2-dimethyl-propionic acid methyl ester (19.00 g, 70%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.55 (d, 1H), 7.26–7.22 (m, 1H), 6.87–6.80 (m, 2H), 4.02 (s, 2H), 3.72 (s, 3H), 1.40 (s, 6H).

Provenance & Evidence