o-Xylyl bromide → Ethyl (2-methylbenzylthio)acetate

HRID 477355

Reaction equation

HRID 477355 reaction equation
C[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Br[CH2:17]C1C=CC=CC=1C.CC[O-].[Na+].SCC(OCC)=O>C(O)C>[CH3:17][C:4]1[CH:3]=[CH:2][CH:15]=[CH:14][C:5]=1[CH2:6][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 6992o-Xylyl bromideHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 4107274Ethyl (4-methylbenzylthio)acetate

Product 1

HCID 13245059Ethyl (2-methylbenzylthio)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-bromomethyltoluene (10 g), a 2M ethanolic solution of sodium ethylate (30 cc) and ethyl 2-mercaptoacetate (6.5 g), in ethanol (100 cc). Ethyl (2-methylbenzylthio)acetate (8.9 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-997824891c5f4fe9bb0d2f23778876aa
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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