Ethyl bromoacetate → HCID 62648051, compound

HRID 602781Notes

Reaction equation

HRID 602781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:11]([O:13][C:14](=[O:17])[CH2:15]Br)C>CN(C=O)C>[CH3:11][O:13][C:14](=[O:17])[CH2:15][S:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 162573-ChlorothiophenolHCID 24758Sodium hydride

Product 1

HCID 62648051HCID 62648051, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 81.1, 4.34 g (0.030 mol) of 3-chloro-benzenethiol in 50 mL of DMF at 0° C. were treated with 1.32 g (0.033 mol, 1.1 eq) of NaH (55% in oil) over 45 min. 4.82 g (0.032 g, 1.05 eq) of bromo-acetic acid ethyl ester were added, and stirring was continued for 2 hours. Workup and purification gave 5.9 g (91%) of (3-chloro-phenylsulfanyl)-acetic acid methyl ester as a colorless oil.

Workup

  1. customWorkup and purification

Sources & evidence

ORD record
ord-a1e9d264b065418b871376ef72d1982c
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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