Water → Methyl 2-chloro-6-fluorobenzoate

Participants

Reaction Steps

An oven-dried round bottom flask successively purged and evacuated with N2 was charged with anhydrous THF (84 ml) and placed in a −78° C. dry ice/acetone bath. To this was added n-butyllithium (2.5 M in hexanes) (18 ml, 46 mmol) and the mixture was stirred for 10 min before adding 1-chloro-3-fluorobenzene (5.48 g, 42.0 mmol) neat. The solution was stirred for 2 hrs before adding neat methyl chloroformate (4.0 ml, 50 mmol). The resultant solution was stirred at −78° C. for 3 hrs and then allowed to warm to RT. Water was added followed by EtOAc. The layers were separated and the aqueous layer was extracted three times with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as a clear liquid.

Provenance & Evidence