Thiophosgene → tert-Butyl 4-isothiocyanatobenzoate

Participants

Reaction Steps

t-Butyl-4-aminobenzoate 1, (25.0 gm, 129.4 mmol) was taken into CHCl3 (250 ml) and saturated NaHCO3 (100 ml) in ice bath. To the stirred mixture thiophosgene (9.9 ml, 129.4 mmol) was added dropwise, and stirring continued for another 90 min. at room temperature after addition was complete. The organic layer was washed with water, dried over Na2SO4, and further purified by column chromatography to provide 28.3 gm of 4-isothiocyanato-benzoic acid t-butyl ester 2.

Provenance & Evidence