4-Bromophenol → 3-Phenylacrylic acid 4-bromophenyl ester

HRID 50588Notes

Reaction equation

HRID 50588 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](Cl)(=[O:18])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 7592203-Phenylacrylic acid 4-bromophenyl esterYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cooled solution of 4-bromophenol (69.2 g) and cinnamoyl chloride (66.8 g) in dichloromethane (150 ml) was treated with triethylamine (40.6 g). After stirring for 18 hrs at room temperature the mixture was washed with water (250 ml), 1 M aqueous HCl, and dried over anhydrous sodium sulphate. Evaporation in vacuum left solid 3-phenylacrylic acid 4-bromophenyl ester (121.0 g, 99.8% yield), m.p. 113.3° C., tlc: (1) 0.83. NMR (CDCl3): 116.85, 118.87, 123.49, 128.38, 129.06, 130.90, 132.49, 134.02, 147.07, 149.84, 165.06.

Workup

  1. washwas washed with water (250 ml), 1 M aqueous HCl
  2. dry with materialdried over anhydrous sodium sulphate
  3. customEvaporation in vacuum

Sources & evidence

ORD record
ord-8d6a8a1244c4468eba95abf34ef735b3
Source dataset
uspto-grants-2004_03
Patent number
US06713464B1

Reaction notes

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