Methyl 2-iodo-4-(trifluoromethyl)benzoate → 2-Cyclohexyl-4-trifluoromethyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 300 mg (0.909 mmol) 2-iodo-4-trifluoromethyl-benzoic acid methyl ester, 14.4 mg (0.0455 mmol) Pd(dppf)Cl2 and 10.6 mg (0.0545 mmol) copper (I) iodide in THF (5 ml) was added at room temperature 2.73 ml (1.364 mmol) cyclohexylzinc bromide (0.5M). The mixture was stirred for 3 hours. Then it was heated to 50° C. and stirred for 4 hours and at room temperature over night. The mixture was concentrated in vacuo and dissolved in ethyl acetate. Then it was washed twice with a 1N HCl solution, twice with a saturated sodium bicarbonate solution and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica (Eluent: heptane/ethyl acetate 0 to 20%) to provide 176 mg (68%) of the title compound as a light yellow oil. MS (m/e): 286 (MH+).

Provenance & Evidence