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

HRID 602776Notes

Reaction equation

HRID 602776 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]([O:12][C:13](=[O:16])[CH2:14]Br)[CH3:11]>CN(C=O)C>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:11]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 7969ThiophenolHCID 24758Sodium hydride

Product 1

HCID 97312Acetic acid, (phenylthio)-, ethyl esterYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.8 g (0.098 mol) of benzenethiol in 70 mL of DMF at 0° C., were treated with 4.31 g (0.108 mol, 1.1 eq) of NaH (55% in oil) over 40 min. 17.19 g (0.103 mol, 1.05 eq) of bromo-acetic acid ethyl ester were added, and stirring was continued over night. The reaction mixture was partitioned between aqueous NH4Cl and EtOAc, dried over Na2SO4, filtered and evaporated, to afford 15.4 g (80%) of phenylsulfanyl-acetic acid ethyl ester as a colorless oil, MS: 197 (MH+).

Workup

  1. waitwas continued over night
  2. customThe reaction mixture was partitioned between aqueous NH4Cl and EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-323e1a1b273e450cbcc11948166bb157
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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