Tributylstannane → 1-Bromo-2-(2,2,2-trifluoroethyl)benzene

HRID 1094811Notes

Reaction equation

HRID 1094811 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](OC(N1C=CN=C1)=S)[C:9]([F:12])([F:11])[F:10].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 57582364O-[1-(2-Bromophenyl)-2,2,2-trifluoroethyl] 1H-imidazole-1-carbothioate

Product 1

HCID 457904731-Bromo-2-(2,2,2-trifluoroethyl)benzeneYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of imidazole-1-carbothioic acid O-[1-(2-bromophenyl)-2,2,2-trifluoroethyl]-ester (Preparation 56, 27.0 g, 73.8 mmol) in toluene (400 ml) was heated at reflux and treated with tri-n-butyltin hydride in three portions: 22 g (75.6 mmol) at first, an additional 10 g (34.4 mmol) after 30 min, and finally 11 g (37.8 mmol) 30 min later. After the addition, the mixture was heated at reflux for another 30 min. The reaction mixture was cooled then the product was distilled at 25 Pa, 60-100° C. to afford the title compound as a colourless oil (17.0 g, 59%).

Workup

  1. temperatureat reflux
  2. customfinally 11 g (37.8 mmol) 30 min
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux for another 30 min
  6. temperatureThe reaction mixture was cooled
  7. distillationthe product was distilled at 25 Pa, 60-100° C.

Sources & evidence

ORD record
ord-7b92846416f54a358a6c43e185f2430a
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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