Toluene → [3-(4-Trifluoromethylphenyl)phenyl]cyclopentyl sulfide

HRID 1635722Notes

Reaction equation

HRID 1635722 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[CH:14]1([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:24]2[CH:25]=[C:20]([S:19][CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:21]=[CH:22][CH:23]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 221708791-Bromo-3-(cyclopentylthio)benzene

Product 1

HCID 17808972[3-(4-Trifluoromethylphenyl)phenyl]cyclopentyl sulfideYield 78%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.0 g (5.2 mmol) of 4-trifluoromethylphenyl boronic acid, 1.4 g (5.4 mmol) of 3-bromophenyl cyclopentyl sulfide, 1.6 g (15.0 mmol) of sodium carbonate and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine) palladium were added to a solvent mixture of 50 ml of toluene, 25 ml of ethanol and 25 ml of water and refluxed under heating and stirring for 2 hours. The resulting reaction mixture was poured into ice-cold water and extracted with toluene. The toluene layer was washed with water twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 1.3 g of [3-(4-trifluoromethylphenyl)phenyl]cyclopentyl sulfide (yield 78.0%) as a colorless liquid (nD20 1.5732).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating
  3. customThe resulting reaction mixture
  4. additionwas poured into ice-cold water
  5. extractionextracted with toluene
  6. washThe toluene layer was washed with water twice
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-70412866f4b043599a535c5712ce26f9
Source dataset
uspto-grants-2003_01
Patent number
US06509354B1

Reaction notes

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