Formamide → HCID 86641783, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 16.2 is prepared in analogy to a published literature procedure (Chem. Lett. 1988, 9, 1531-1534). A mixture of 3-chloro-2-fluorobenzaldehyde (2.00 g, 12.6 mmol), p-toluenesulfinic acid (2.96 g, 18.9 mmol), TMSCl (1.75 mL, 13.9 mmol) and formamide (1.25 mL, 31.5 mmol) in toluene (7 mL) and CH3CN (7 mL) is heated at 50° C. for 5h. After completion, the reaction mixture is quenched by H2O, EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; HPLC: AtRet=4.21 min; 1HNMR(CDCl3) 8.18 (s, 1H), 7.72 (d, 2H), 7.50-7.45 (m, 1H), 7.40-7.30 (m, 3H), 7.20-7.10 (m, 1H), 7.00 (d, 1H), 6.60 (d, 1H), 2.45 (s, 3H).

Provenance & Evidence