Ethyl Acetate → HCID 68001502, compound

HRID 1503090Notes

Reaction equation

HRID 1503090 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH:10]([CH2:16]C)[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:18]([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:10]([CH3:16])([CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 805982-Bromobenzenethiol

Product 1

HCID 68001502HCID 68001502, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromothiophenol (0.99 g, 5.0 mmol), ethyl 2-bromobutyrate (1.17 g, 6.0 mmol) and K2CO3 (0.966 g, 7.0 mmol) in DMF (2 mL) was stirred at room temperature for 2 hours. Ethyl acetate was added and the organic phase washed with brine, dried (MgSO4), concentrated and purified by chromatography to yield ethyl 2-(2-bromophenylthio)-2-methylpropanoate (1.34 g, 84%).

Workup

  1. washthe organic phase washed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-13fe321ccf204deb9b6e5e2925742174
Source dataset
uspto-grants-2015_12
Patent number
US09212135B2

Reaction notes

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