3-Chloro-2-chloromethyl-1-propene → HCID 66831285, compound

Participants

Reaction Steps

To a solution of MeOH at 0 C under N2 was added Na metal (1.03 g, 45 mmol). The reaction was slowly allowed to warm to room temperature. 4-hydroxy-4′mercaptobiphenyl (8.0 g, 40 mmol) was added to the reaction, and the reaction was heated to reflux. 3-chloro-2-chloromethyl propene (2.25 g, 18 mmol) was added dropwise over an hour, and the reaction was allowed to reflux overnight. The solution was reduced in vacuo and purified by flash chromatography 20:80 acetone/hexanes to yield 3.92 g of the pure allyl sulfide. Yield 47.7%. 1H NMR (400 MHz, DMSO-d6, δ): 9.56 (s, 2H, Ar—OH), 7.46 (m, 8H, Ar—H), 7.33 (m, 4H, Ar—H), 6.82 (m, 4H, Ar—H), 5.06 (s, 2H, C═CH2), 3.8 (s, 4H); 13C NMR (400 MHz, DMSO-d6, δ): 157.13 (C1), 139.57 (C10), 137.92 (C5), 133.15 (C8), 129.97 (C4), 129.52 (C7), 127.43 (C3), 126.24 (C6), 116.55 (C11), 115.71 (C2) 36.89 (C9); MS (ESI, m/z): [M−H]− calcd for C28H24O2S2, 455.1; found, 455.1.

Provenance & Evidence