Tert-Butylamine → 5-[(Tert-butylamino)sulfonyl]-2-chloro-4-fluorobenzoic acid

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Reaction Steps

tert-Butyl amine (77 mL, 0.7 mol, 10 equiv) was added to 300 mL dioxane at 0° C. Ice chips were added to the flask for several minutes before the addition of 2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid (20 g, 73.24 mmol, 1 equiv). Both the internal and external temperature of the reaction was maintained at or below 0° C. for 2 h. The reaction was then concentrated half-way and acidified to pH 2 with 1N HCl. The product was extracted into EtOAc. The organics were dried over Na2SO4, filtered and concentrated down to give 2-chloro-5-{[(1,1-dimethylethyl)amino]sulfonyl}-4-fluorobenzoic acid 883-4a as a brown solid (21 g; 92% yield).

Provenance & Evidence