Ethyl 4-bromobutyrate → Ethyl 4-(methylthio)butyrate

HRID 227456Notes

Reaction equation

HRID 227456 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:10][S-:11].[Na+]>CN(C)C=O>[CH3:10][S:11][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 4378561Sodium methanethiolate

Product 1

HCID 5463935Ethyl 4-(methylthio)butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 4-bromobutyrate (0.269) in N,N-dimethylformamide (3 ml) was treated with sodium thiomethoxide (0.103 g), and the mixture stirred at room temperature overnight. The mixture was partitioned between water (10ml) and dichloromethane (10 ml), and the organic layer was washed with 1:1 saturated aqueous sodium chloride and water (10 ml). The organic layers were evaporated in vacuo to give the title compound as a clear oil (0.135 g).

Workup

  1. customThe mixture was partitioned between water (10ml) and dichloromethane (10 ml)
  2. washthe organic layer was washed with 1:1 saturated aqueous sodium chloride and water (10 ml)
  3. customThe organic layers were evaporated in vacuo

Sources & evidence

ORD record
ord-8f19baae2ee7415dbd53688f2a271aa2
Source dataset
uspto-grants-2009_07
Patent number
US07560548B2

Reaction notes

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