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

HRID 726849Notes

Reaction equation

HRID 726849 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:24])[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][O:14][CH2:15][F:16].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:9][O:10][C:11](=[O:24])[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][Br:1])=[CH:13][O:14][CH2:15][F:16]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 544607813-Fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester

Product 1

HCID 543314062-(2-Bromomethylphenyl)-3-fluoromethoxyacrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Preparation of ##STR7## 11.75 g of N-bromosuccinimide are added in several small portions, under reflux, to a solution of 14.75 g of 3-fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester and 0.53 g of dibenzoyl peroxide in 90 ml of carbon tetrachloride and then the mixture is refluxed for a further 0.5 hour. The suspension is cooled to room temperature, filtered and concentrated to dryness by evaporation. Chromatography on silica gel with hexane/ethyl acetate (6:1) yields pure 2-(2-bromomethylphenyl)-3-fluoromethoxy-acrylic acid methyl ester; m.p. 73°-76° C.

Workup

  1. additionare added in several small portions
  2. temperaturethe mixture is refluxed for a further 0.5 hour
  3. filtrationfiltered
  4. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-e49c3fdb88eb4abbbdb6deb09f4b9df0
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

Loading…