Bromotrifluoromethane → 2-(Trifluoromethylthio)biphenyl

HRID 974066

Reaction equation

HRID 974066 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+].[F:16][C:17](Br)([F:19])[F:18]>CN(C)C=O>[F:16][C:17]([F:19])([F:18])[S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6384Bromotrifluoromethane3×HCID 24758Sodium hydrideHCID 27604132-Phenylthiophenol

Product 1

HCID 109230652-(Trifluoromethylthio)biphenylYield 87.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction tube in a photoreaction apparatus was charged with 50 ml of dimethylformamide (DMF) and 5.59 g (30 mmol) of 2-mercaptobiphenyl, and with ice cooling and stirring, 1.2 g (30 mmol) of sodium hydride (60% in oil) was added. When foaming ceased, trifluoromethyl bromide was introduced into the reaction solution. The atmosphere within the reaction system was replaced by gaseous trifluoromethyl bromide, and while irradiating light from a high-pressure mercury lamp, about 2 equivalents of trifluoromethyl bromide was passed into the reaction system over about 2 hours. Ice water (150 ml) was added to the resulting brown reaction solution, and it was extracted with pentane. The organic layer was washed with water and then with saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give 6.71 g (87.9%) of 2-(trifluoromethylthio)biphenyl as an oil. It was purified by silica gel column chromatography. The properties of the product were as shown below.

Workup

  1. customwhile irradiating light from a high-pressure mercury lamp
  2. extractionwas extracted with pentane
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  5. customThe anhydrous magnesium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-edb37228608e4725b18afee3f1e45907
Source dataset
uspto-grants-1991_11
Patent number
US05066795

Linked notes

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