Formamide → N-((2,5-Difluorophenyl)(tosyl)methyl)formamide

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 4-methylbenzenesulfinic acid (5.00 g, 32.0 mmol, Preparation #3, Step A), (1S)-(+)-10-camphorsulfonic acid (0.074 g, 0.32 mmol), 2,5-difluorobenzaldehyde (3.83 mL, 35.2 mmol) and formamide (6.38 mL, 160 mmol). The reaction mixture was stirred at about 65° C. for about 16 h. The reaction mixture had solidified overnight. The solid was broken up and suspended in MeOH. The chunks of solid were ground to a powder with a spatula and the solid was filtered and washed with MeOH. The filter cake was dried under vacuum at about 60° C. to give the title compound (5.92 g, 56.8%) as a white powder. LC/MS (Table 1, Method a) Rt=2.37 min; MS m/z: 343.1 (M+NH3)+.

Provenance & Evidence