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

HRID 1823156노트

반응식

HRID 1823156 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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). 1H-NMR data (300 MHz, CDCl3 solvent, δ value)

후처리

  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

출처 및 근거

ORD 기록
ord-8ad04b0a098a4d75bc2b47f4832fffbf
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037930B2

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