Sulfuric Acid → 3-iodo-5-(trifluoroMethyl)phenol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-amino-5-(trifluoromethyl)phenol (42 g, 237.12 mmol, 1.00 equiv) in water (80 mL) at 0° C. was added 50% sulfuric acid (240 mL) dropwise. The resulting solution was stirred at 0° C. for 30 min. A solution of sodium nitrite (24.5 g, 355.07 mmol, 1.50 equiv) in water (90 mL) followed by a solution of potassium iodide (78.7 g) in water (80 mL) was added dropwise at 0° C. The resulting solution was stirred at 25° C. for 8 h. The reaction mixture was extracted with 2×100 mL of ethyl acetate. The combined organic layers were washed with 2×150 mL of saturated Na2SO3 solution and 2×200 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrate under reduced pressure. The residue was purified on a silica gel column eluted with 0-7% of ethyl acetate in petroleum ether to give 54 g (79%) of 3-iodo-5-(trifluoromethyl)phenol as a yellow oil.

Provenance & Evidence