Methanol → Methyl 3-bromocinnamate, predominantly trans

HRID 1524283Notes

Reaction equation

HRID 1524283 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12]([OH:14])=[O:13].[CH3:18]O>>[CH3:18][O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:9]1[CH:15]=[CH:16][CH:17]=[C:7]([Br:6])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 362513-(3-Bromophenyl)acrylic acid

Product 1

HCID 1482751Methyl 3-bromocinnamate, predominantly trans

Procedure

Add concentrated sulfuric acid (5.0 mL, 90 mmol) to a solution of 3-bromocinnamic acid (25.0 g, 110 mmol) in MeOH (250 mL). Heat the mixture to reflux for 5 h then cool to room temperature and concentrate under reduced pressure. Dilute the residue with water and extract with EtOAc. Concentrate the combined organic phase under reduced pressure and purify the residue by silica gel chromatography to provide 26 g of trans-3-(3-bromo-phenyl)-acrylic acid methyl ester.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 5 h
  3. concentrationconcentrate under reduced pressure
  4. additionDilute the residue with water
  5. extractionextract with EtOAc
  6. concentrationConcentrate the combined organic phase under reduced pressure
  7. custompurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-dd0fb5823d42412abc408cdcb7cf1514
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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