Benzoyl Peroxide → 2-(2-Bromomethylphenyl)-3-difluoromethoxy-acrylic acid methyl ester

HRID 726851Notes

Reaction equation

HRID 726851 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[CH:5][O:6][CH:7]([F:9])[F:8].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][Br:36])=[CH:5][O:6][CH:7]([F:8])[F:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 538491443-Difluoromethoxy-2-(o-tolyl)acrylic acid methyl ester

Product 1

HCID 537631492-(2-Bromomethylphenyl)-3-difluoromethoxy-acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 14.2 g of 3-difluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester and 0.15 g of dibenzoyl peroxide in 85 ml of carbon tetrachloride is heated to reflux. With radiation from a lamp, 10.44 g of N-bromosuccinimide are then added in several small portions and the reaction mixture is left to react for 1.5 hours. After cooling to room temperature, the reaction mixture is filtered and concentrated by evaporation in vacuo. The pale red crude product is purified by chromatography on silica gel with hexane/ethyl acetate and crystallised from hexane. Pure 2-(2-bromomethylphenyl)-3-difluoromethoxy-acrylic acid methyl ester is obtained; m.p. 63°-67° C.

Workup

  1. waitthe reaction mixture is left
  2. customto react for 1.5 hours
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe pale red crude product is purified by chromatography on silica gel with hexane/ethyl acetate
  6. customcrystallised from hexane

Sources & evidence

ORD record
ord-0cc6366f25ff4e0c9709b9b9f53f9658
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

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