Phenethyl bromide → Ethyl (phenethylthio)acetate

HRID 477345

Reaction equation

HRID 477345 reaction equation
CC1C=CC(C[S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=CC=1.Br[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC[O-].[Na+].SCC(OCC)=O>C(O)C>[CH2:17]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 4107274Ethyl (4-methylbenzylthio)acetate

Product 1

HCID 304016Ethyl (phenethylthio)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure is as in Example 29 for the preparation of ethyl (4-methylbenzylthio)acetate, starting with (2-bromoethyl)benzene (20 g), a 2M ethanolic solution of sodium ethylate (25 cc) and ethyl 2-mercaptoacetate (13 g) in ethanol (150 cc). Ethyl (phenethylthio)acetate (21.7 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-608641d1636e426c8d2437c2f86e5d34
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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