2-Methylbenzoic acid → 4-Bromo-2-methylbenzoic acid

Participants

Reaction Steps

Chill a mixture of 140 gm. (0.875 mole) of bromine and 2.45 gm. of iron powder in an ice-bath and add portionwise during 15 minutes 93.31 gm. (0.7 mole) of o-toluic acid. Remove the reaction flask from the ice-bath and stir for 2 hours. Allow the resulting mushy solid to stand at room temperature overnight. Flush the reaction mixture with nitrogen. Finely grind the resulting solid cake, wash with water, aqueous sodium thiosulfate solution, water and dry to obtain the title compound together with the 3-bromo isomer (yield 144.7 gm., m.p. 112°-148° C.). The product is employed in the next step without further purification.

Provenance & Evidence