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

HRID 716675Notes

Reaction equation

HRID 716675 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:16][C:17](CCl)=[CH2:18]>CO>[CH2:18]([S:14][CH2:11][CH:12]=[CH2:13])[CH:17]=[CH2:16].[C:5]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 18769550HCID 18769550, compound

Product 1

HCID 66831285HCID 66831285, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureto reflux overnight
  3. custompurified by flash chromatography 20:80 acetone/hexanes

Sources & evidence

ORD record
ord-ccbfc9141d5344ffb8997499a5a83f1b
Source dataset
uspto-grants-2015_11
Patent number
US09193682B2

Reaction notes

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