Methanol → Methyl [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetate

HRID 2192904Notes

Reaction equation

HRID 2192904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:11][CH2:10]1.S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([O:15][CH3:21])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59570913[3-Bromo-4-(cyclopropylsulfanyl)phenyl]acetic acid

Product 1

HCID 59571017Methyl [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetate

Procedure

A mixture of [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetic acid (13.5 g), concentrated sulfuric acid (0.135 mL), and methanol (40 mL) was stirred under heating and reflux for 4 hours. After leaving to be cooled at room temperature, the solvent was evaporated under reduced pressure, and then a 1 M aqueous sodium hydroxide solution (100 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (100 mL×3). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure to obtain methyl [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetate (13.8 g) as a colorless solid.

Workup

  1. temperatureunder heating
  2. temperaturereflux for 4 hours
  3. customAfter leaving
  4. customthe solvent was evaporated under reduced pressure
  5. additiona 1 M aqueous sodium hydroxide solution (100 mL) was added to the reaction mixture
  6. extractionfollowed by extraction with ethyl acetate (100 mL×3)
  7. washThe organic layer was washed with saturated brine (100 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-4f50fde4359543a79bf66083b00d5965
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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