Methanol → Methyl 4-bromocinnamate

HRID 1892153

Reaction equation

HRID 1892153 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:17])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 99777p-Bromocinnamic acid

Product 1

HCID 816774Methyl 4-bromocinnamate

Procedure

To a stirred solution of 4-bromocinnamic acid (16 g) in methanol (150 mL) was added thionyl chloride (30 mL) at 0° C. The reaction mixture was warmed to room temperature and refluxed for 3 hours. After cooling to room temperature the solvents were evaporated to dryness. The crude compound obtained was used as such for the next step.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling to room temperature the solvents
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-1453db34cac84fa79f365c1ae16913b0
Source dataset
uspto-grants-2013_08
Patent number
US08507670B2

Linked notes

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