Ethyl bromoacetate → Acetic acid, (butylthio)-, ethyl ester

HRID 477367Notes

Reaction equation

HRID 477367 reaction equation
[C:1]1([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])C=C[CH:4]=[CH:3][CH:2]=1.C(S)CCC.CC[O-].[Na+].BrCC(OCC)=O>C(O)C>[CH2:1]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8012ButanethiolHCID 97312Acetic acid, (phenylthio)-, ethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 10749796Acetic acid, (butylthio)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure is as in Example 2 for the preparation of ethyl (phenylthio)acetate, starting with n-butylmercaptan (10.7 cc), a 2M ethanolic solution of sodium ethylate (50 cc) and ethyl bromoacetate (16.7 g) in ethanol (100 cc). Ethyl (n-butylthio)acetate (15.4 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-7518eede966246c28649c125fa10cb27
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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