Ethyl Acetate → (S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

HRID 1432107Notes

Reaction equation

HRID 1432107 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9]Br)[CH:3]=1.C([S:14][CH2:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])(=O)C.[OH-].[Na+].CCOC(C)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH2:9][S:14][CH2:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2724506D-beta-acetylthioisobutyric acidHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

Product 1

HCID 68541731(S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.55 g (21 mmol) 1-bromo-3-bromomethyl-5-methyl-benzene and 2.90 ml (21 mmol) (S)-3-acetylsulfanyl-2-methyl-propionic acid in 32 ml methanol is cooled in an ice bath and 4N aqueous sodium hydroxide (15.8 ml, 63 mmol) are added. The reaction mixture is stirred at rt for 3 hrs. EtOAc is added to the mixture and the organic layer is washed with water and brine and evaporated. Filtration over silica gel (flashmaster, hexane to hexane/EtOAc 4/6) gives the title compound.

Workup

  1. washthe organic layer is washed with water and brine
  2. customevaporated
  3. filtrationFiltration over silica gel (flashmaster, hexane to hexane/EtOAc 4/6)

Sources & evidence

ORD record
ord-25d74e1d243940ddb7790c5ebb43d38c
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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