Sodium Hydroxide → 2-Chloro-4-fluoro-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

Bromine (7.61 mL, 148 mmol) was added dropwise to sodium hydroxide (19.70 g, 492 mmol) dissolved in Water (80 mL) maintaining temperature<10° C. 1-(2-chloro-4-fluoro-3-methylphenyl)ethanone (I73) (9.19 g, 49.2 mmol) dissolved in 1,4-dioxane (80 mL) was added dropwise at 0° C. and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with chloroform (2×20 mL) and the aqueous phase acidified to pH1 with concentrated hydrochloric acid. The resulting precipitate was filtered, washed with water, a little diethyl ether (Note: product has some ether solubility) and dried to afford product in 8.89 g. This was recrystalised from toluene to afford product in 6.25 g as fine white needles.

Provenance & Evidence