Ammonium Chloride → 4,4,4-Trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-ol

HRID 1427508노트

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HRID 1427508 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[F:23][C:24]([F:30])([F:29])[CH2:25][CH2:26][CH:27]=[O:28].[NH4+].[Cl-]>C1COCC1>[F:23][C:24]([F:30])([F:29])[CH2:25][CH2:26][CH:27]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[OH:28]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 27770834,4,4-TrifluorobutanalHCID 127123494-Bromo-4'-(trifluoromethyl)biphenylHCID 178418339Butyllithium

생성물 1

HCID 866673024,4,4-Trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-ol수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

n-Butyllithium (150 uL of a 2.5M solution in hexanes, 0.38 mmol) was added dropwise to a −78° C. solution of 4-bromo-4′-(trifluoromethyl)biphenyl (113 mg, 0.375 mmol) in 3 mL THF. The resulting solution was stirred at −78° C. 15 min. 4,4,4-trifluorobutyraldehyde (98 mg, 0.78 mmol) was added neat. The resulting colorless solution was stirred at −78° C. 20 min. 1 mL sat. aqueous NH4Cl was added, and the mixture warmed to room temperature. The reaction mixture was partitioned between Et2O and water. The organic layer was dried over MgSO4 and concentrated to give a colorless oil. The crude material was purified by silica gel chromatography to provide 4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butan-1-ol (87 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 7.64-7.71 (m, 4H), 7.57-7.62) m, 2H), 7.41-7.47 (m, 2H), 4.78-4.87 (m, 1H), 2.10-2.39 (m, 3H), 1.96-2.09 (m, 1H).

후처리

  1. custom15 min
  2. stirringThe resulting colorless solution was stirred at −78° C
  3. custom20 min
  4. temperaturethe mixture warmed to room temperature
  5. customThe reaction mixture was partitioned between Et2O and water
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customto give a colorless oil
  9. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-61f4ba8e234940418b0dacb1a222e339
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933104B2

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