Benzyl mercaptan → HCID 86746478, compound

HRID 1646270Notes

Reaction equation

HRID 1646270 reaction equation
[Cl:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](O)=[O:6].[CH2:10]([SH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([S:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 8857Ethyl AcetateHCID 19392432HCID 19392432, compound

Product 1

HCID 86746478HCID 86746478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4.0 g of 4-chloro-4,4-difluorobutyric acid are added dropwise over the course of 45 minutes to a solution of 4.5 g of N,N'-carbonyldiimidazole in 30 ml of dimethylformamide at 0° C. After the solution has been stirred at 0° C. for 2 hours, 2.82 g of benzyl mercaptan are added and the mixture is allowed to warm to room temperature over the course of 17 hours. Then 100 ml of ethyl acetate are added and the organic solution is washed with saturated sodium chloride solution. The organic phase is dried over MgSO4 and evaporated. The resulting crude product is purified by chromatography on silica gel (mobile phase: hexane/ethyl acetate 9:1). This results in 4.0 g of S-benzyl 4-chloro-4,4-difluorothiobutyrate as an oil, nD20 : 1.5220.

Workup

  1. temperatureto warm to room temperature over the course of 17 hours
  2. washthe organic solution is washed with saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated
  5. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: hexane/ethyl acetate 9:1)
  6. customThis results in 4.0 g of S-benzyl 4-chloro-4,4-difluorothiobutyrate as an oil

Sources & evidence

ORD record
ord-159eaef8b652493ba0d7be60f934cce3
Source dataset
uspto-grants-1993_01
Patent number
US05179121

Reaction notes

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