4-(Bromomethyl)benzoic acid → Tert-butyl 4-(bromomethyl)benzoate

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Reaction Conditions

Reaction Steps

p-Bromomethyl benzoic acid (8.1 g) was refluxed with α,α dichloromethyl methyl ether (50 mL) for 1 h. The reaction mixture was evaporated to dryness, co-distilled with toluene twice and pumped under high vacuum. To the acid chloride redissolved in THF (100 mL) at −78° C. was added potassium tert-butoxide 1M in THF (30 mL) dropwise. Then temperature was raised to −20° C. and stirred for 1 h. The reaction mixture was quenched with NH4OAc and extracted with EtOAc. The organic phase was dried over Na2SO4 and evaporated to yield 50 g of tert-butyl-4-(bromomethyl)benzoate.

Provenance & Evidence