Triethylamine → (3-Iodophenyl)(isocyano)methyl 4-methylphenyl sulfone

Participants

Reaction Conditions

Reaction Steps

POCl3 (3.05 mL) was added to a stirred solution of {(3-iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide (Intermediate 52) (6.23 g) in dry THF (35 mL) at 25° C. and stirred for 5 minutes. The reaction mixture was cooled to 0° C. and Et3N (13.7 mL) was added dropwise over 45 minutes, keeping the internal temperature below 10° C. The reaction mixture was allowed to stir at 5-10° C. for a further 45 minutes. EtOAc (140 mL) and water (140 mL) was added and then stirred for 5 minutes. The organic phase was washed with water (2×140 mL), NaHCO3 (sat. aq., 140 mL) and then brine (140 mL). The organic phase was concentrated in vacuo to afford a dark brown gum. This was then passed through a pad of silica washing with DCM and concentrated in vacuo to afford a dark brown gum (ca. 70% pure 3.5 g, 58%);

Provenance & Evidence