Thionyl Chloride → HCID 66742926, compound

Participants

Reaction Steps

To a solution of 2,4,6-trifluoro-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide (43.8 g, 177.1 mmol) in dry dichloromethane (400 mL) was added thionyl chloride (58.9 ml, 415 mmol) via slow drop-wise addition over 25 minutes (reaction flask was immersed in an ice bath part way through the addition to control the temperature). After complete addition the material was stirred at ambient temperature over night. The volume was reduced to 30% by concentration under vacuum. To that was added ether (200 ml) and a solid precipitate (39.94 g off-white solid) was collected by filtration. The ether filtrate was set aside and the solid material was taken up in water (120 ml) and treated with an aqueous solution of sodium hydroxide (2N, 55 ml). Ethyl acetate (120 ml) was added and the mixture was transferred to a separatory funnel and shaken. The organic phase was collected and washed with an equal volume of water. The ethyl acetate phase was collected and the aqueous phases were back extracted with ethyl acetate (2×100 ml). The combined organic phases were dried (magnesium sulfate), filtered and concentrated in vacuo to provide the desired as a pure off-white solid (33.98 g). (M+H)+=230 m/e.

Provenance & Evidence