Potassium Carbonate → HCID 20542843, compound

HRID 2374052Notes

Reaction equation

HRID 2374052 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1>C(#N)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 680214-Fluorobenzyl bromide

Product 1

HCID 20542843HCID 20542843, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-mercaptoacetate (Aldrich, 1.0 mL, 9.1 mmol) in acetonitrile (10.0 mL) were added K2CO3 (2.76 g, 20.0 mmol) and 1-(bromomethyl)-4-fluorobenzene (2.27 g, 12.0 mmol). The mixture was stirred at room temperature for 12 h. After filtration and concentration, the residue was purified by flash column chromatography on SiO2 to give ethyl 2-(4-fluorobenzylthio)acetate (1.89 g, 91% yield). MS(ESI+): m/z 251.08 (M+H)+.

Workup

  1. filtrationAfter filtration and concentration
  2. customthe residue was purified by flash column chromatography on SiO2

Sources & evidence

ORD record
ord-57e4b0dbdd8e4bb99d8063b214d9bc2a
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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