Bromochloromethane → 1-((Chloromethyl)sulfonyl)naphthalene

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-naphthalene sulfonyl chloride (20.2 g, 89.1 mmol), sodium sulfite (22.5 g, 178 mmol) and sodium bicarbonate (15.1 g, 180 mmol) in water was stirred at 100° C. for one hour, allowed to cool to ambient temperatures for 40 minutes, treated with bromochloromethane (90 mL, 1.4 mol) and tetrabutylammonium bromide (2.87 g, 8.91 mmol), stirred at 75° C. for 14.5 hours and cooled to ambient temperatures. The phases were separated and the organic phase was concentrated in vacuo. The resultant residue was purified by flash chromatography with 100% ethyl acetate to give 1-chloromethanesulfonyl-naphthalene as a pale yellow solid, 19.0 g (88.8% yield), mp 103-5° C., Mass Spectrum (+EI, M+) m/z 240. 1HNMR (500 MHz, DMSO-d6): δ8.64-5 (m, 1H), 8.41 (d, 1H, J=8.23 Hz), 8.27 (dd, 1H, J=7.33 Hz and 1.22 Hz), 8.16-8.18 (m, 1H), 7.71-7.81 (m, 3H), 5.40 ppm, (s, 2H). Elemental Analysis for C11H9ClO2S: Calcd: C, 54.89; H, 3.77; N, 0.00; Found: C, 54.98; H, 3.81; N, 0.00.

Provenance & Evidence