Acetic Acid → 2-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of chloromethylphenyl sulfone (10.51 g, 55.13 mmol) in THF (110 mL) was added 5.9 mL (56 mmol) of 1-fluoro-4-nitrobenzene. The reaction mixture was chilled to 0° C., and 1.0 M potassium tert-butoxide in THF (145 mL, 145 mmol) was added dropwise. The reaction mixture was stirred under nitrogen at ambient temperature for one hour. Acetic acid (9 mL, 160 mmol) was then added. The reaction mixture was solvent evaporated and partitioned in brine and ethyl acetate. The organic phase was then dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was stirred in diethyl ether, filtered and dried in vacuo at 73° C. for 12 hours. 2-Benzenesulfonylmethyl-4-fluoro-1-nitrobenzene as a light brown-yellow solid was obtained (10.24 g, 62.8%): MP: 169-171° C.; Mass spectrum (−EI, [M−H]−) m/z 294. 1HNMR (500 MHz, DMSO-d6): δ8.10-8.14 (m, 1H), 7.70-7.75 (m, 1H), 7.56-7.63 (m, 4H), 7.45-7.50 (m, 1H), 7.20 (dd, 1H, J=9.27 Hz and 2.81 Hz), 5.12 ppm (s, 2H). Elemental Analysis for C13H10FNO4S: Calcd: C, 52.88; H, 3.41; N, 4.74; Found: C, 52.63; H, 3.14; N, 4.66;

Provenance & Evidence