Chlorosulfonic acid → 4-Fluoro-3-nitrobenzene-1-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

2-Fluoronitrobenzene (10.0 g, 70.9 mmol) was added to chlorosulfonic acid (10.0 ml, 150 mmol) at 65° C. After stirring at 85° C. for 18 h, the reaction mixture was cooled to room temperature and poured onto ice chips and extracted with CH2Cl2 (2×250 ml). The combined organic extracts were washed with saturated NaHCO3 solution and dried (MgSO4). Concentration at room temperature and then at 100° C. under high vacuum produced 2.40 g (14%) of the title compound as a yellow oil. 1H-NMR (CDCl3): δ 8.76 (1H, dd, J=2.4, 6.5 Hz), 8.33 (1H, ddd, J=2.4, 3.8, 9.2 Hz), 7.61 (1H, t, J=9.2 Hz). MS (EI): 239 (15, M+), 204 (100).

Provenance & Evidence