Methanol → Methyl 4-bromocinnamate

HRID 84043

Reaction equation

HRID 84043 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.[CH3:13]O>S(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:13])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 99777p-Bromocinnamic acid

Product 1

HCID 816774Methyl 4-bromocinnamate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a stirred solution of 4-bromocinnamic acid (16 g) in methanol (150 mL), thionyl chloride (30 mL) was added 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
  3. customthe solvents were evaporated to dryness

Sources & evidence

ORD record
ord-19d071aaad2f46dc9e3ff6d891e31a8b
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Linked notes

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