Benzyl mercaptan → HCID 55106473, compound

HRID 401757Notes

Reaction equation

HRID 401757 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1F)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18]([SH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>CS(C)=O>[CH2:18]([S:25][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[F:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 991663,4-Difluorobenzoic acid

Product 1

HCID 55106473HCID 55106473, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

3,4-Difluorobenzoic acid (964 mg, 6.1 mmol, 1 eq), cesium carbonate (3.97 g, 12.1 mmol, 2 eq) and benzyl mercaptan (763 mg, 6.14 mmol, 1 eq) were combined in dimethyl sulphoxide (5 ml) and the reaction mixture heated at 75° C. for 4 hours. The reaction mixture was poured into ethyl acetate (10 ml) then extracted into water (10 ml). The aqueous phase was acidified with 2M HCl, extracted into ethyl acetate (10 ml), dried over sodium sulphate, filtered and evaporated to yield the title compound as a white solid (1.53 g, 5.83 mmol, 95%).

Workup

  1. extractionthen extracted into water (10 ml)
  2. extractionextracted into ethyl acetate (10 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bdee7c469fe84310935f84ab7211569d
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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