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Benzyl mercaptan → Methyl 4-(benzylthio)-2-chlorobenzoate

HRID 401780
Notes
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Reaction equation

HRID 401780 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](F)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19]([SH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CS(C)=O>[CH2:19]([S:26][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([Cl:1])[CH:11]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2763551Methyl 2-Chloro-4-fluorobenzoate

Product 1

HCID 22387852Methyl 4-(benzylthio)-2-chlorobenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-chloro-4-fluorobenzoate (1.92 g, 10.2 mmol, 1 eq), cesium carbonate (3.74 g, 11.5 mmol, 0.13 eq) and benzyl mercaptan (1.3 g, 10.5 mmol, 1.03 eq) were combined in dimethyl sulphoxide (20 ml) and the reaction mixture heated at 50° C. for 4 hours. The reaction mixture was poured into ethyl acetate (10 ml) then washed with water (10 ml). The organic phase was dried over sodium sulphate, evaporated to yield the title compound as pink oil (2.82 g, 9.63 mmol, 95%).

Workup

  1. washthen washed with water (10 ml)
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-5cee19eed4064bd5adf1a25de284c3d3
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741934B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes