2-BROMO-1-CHLORO-4-(TRIFLUOROMETHOXY)BENZENE → 1-Chloro-2-ethenyl-4-(trifluoromethoxy)benzene

HRID 1267894Notes

Reaction equation

HRID 1267894 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[Cl:13].[CH2:14](C([Sn])=C(CCCC)CCCC)[CH2:15]CC>C1(C)C=CC=CC=1>[Cl:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:7][C:2]=1[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 27614052-BROMO-1-CHLORO-4-(TRIFLUOROMETHOXY)BENZENEHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 185425101-Chloro-2-ethenyl-4-(trifluoromethoxy)benzeneYield 33.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Bromo-1-chloro-4-(trifluoromethoxy)benzene (Description 25; 1.0 g, 3.6 mmol) and tri-n-butylvinyl tin (1.21 g, 3.8 mmol) were dissolved in toluene (20 mL) and the solution was degassed for 45 minutes with nitrogen. Tetrakis(triphenylphosphine) palladium (0) (100 mg) was then added and the solution heated at reflux for 2 hours. Once cooled, the solution was concentrated and the residue was purified by silica chromatography to give the title compound (274 mg, 1.2 mmol).

Workup

  1. customthe solution was degassed for 45 minutes with nitrogen
  2. additionTetrakis(triphenylphosphine) palladium (0) (100 mg) was then added
  3. temperaturethe solution heated
  4. temperatureat reflux for 2 hours
  5. temperatureOnce cooled
  6. concentrationthe solution was concentrated
  7. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-42516b6a83aa443da1d965425cf9656c
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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