Epichlorohydrin → HCID 58150208, compound

Participants

Reaction Steps

4-chlorophenyl-2,5-difluorobenzylsulfone (12 g, 39.6 mmol) in THF (99 ml) was treated with nBuLi (19 ml, 2.5 M in hexane, 47.6 mmol) at 0° C. for 10 min followed by addition of epichlorohydrin (3.73 ml, 47.6 mmol). The reaction was slowly warmed to room temperature for 14 h, quenched with water (100 ml) and diluted with EtOAc (300 ml). The organic phase was separated, dried (Na2SO4) and evaporated to dryness to give an oil. This material was chromatographed on silica, eluting with 10-45% ethyl acetate in hexanes to afford 9.8 g of the desired product as off-white solid. 1H NMR (600 MHZ, CDCl3) two diastereomers (˜1/1) δ 7.52 (m, 2H/2H), 7.38 (m, 2H/2H), 7.30-7.22 (m, 1H/1H), 6.99 (m, 1H/1H), 6.86-6.80 (m, 1H/1H), 4.76-4.70 (m, 1H/1H), 3.03-2.48 (m, 4H/4H), 2.37 (m, 1H), 2.20 (m, 1H). MS calculated 359.0 (MH+), exp 358.9 (MH+).

Provenance & Evidence