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Benzyl Bromide → 3-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile

HRID 1952405
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HRID 1952405 반응식
C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]([F:37])([F:36])[O:15][C:16]1[CH:17]=[C:18]([CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:35])([F:34])[F:33])[CH:26]=2)[C:23]#[N:24])[CH:19]=[CH:20][CH:21]=1.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1COCC1>[C:39]1([CH2:38][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:35])([F:34])[F:33])[CH:26]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][C:14]([F:36])([F:37])[F:13])[CH:17]=2)[C:23]#[N:24])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 594587512,2-Bis(3-(trifluoromethoxy)phenyl)acetonitrileHCID 178418339Butyllithium

생성물 1

HCID 591928133-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile수율 98%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

To a solution of diisopropyl amine (2.48 mL, 17.5 mmol) in THF (60 mL) at −78° C. was added dropwise n-BuLi (1.6 M in hexane, 11.5 mL, 18.3 mmol) and the reaction mixture was stirred for 5 min. A solution of (2,2-bis(3-(trifluoromethoxy)phenyl)acetonitrile (5.51 g, 15.3 mmol), prepared as described in Procedure 14, in THF (5 mL) was added dropwise to the reaction mixture and stirred for 1 h. Benzyl bromide (2.17 mL, 18.3 mmol) was added dropwise, then the cooling bath was removed and the reaction mixture was stirred at rt for 45 min. The reaction mixture was poured into H2O (75 mL) and extracted with diethyl ether (2×75 mL). The combined organic portions were dried over Na2SO4, filtered and concentrated under reduced pressure to yield a residue. The residue was purified on a silica gel ISCO cartridge with elution at 5 to 15% Et2O/hexane to give 3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile (6.75 g, 98% yield) as a clear yellow oil.

후처리

  1. additionwas added dropwise to the reaction mixture
  2. stirringstirred for 1 h
  3. customthe cooling bath was removed
  4. stirringthe reaction mixture was stirred at rt for 45 min
  5. additionThe reaction mixture was poured into H2O (75 mL)
  6. extractionextracted with diethyl ether (2×75 mL)
  7. dry with materialThe combined organic portions were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a residue
  11. customThe residue was purified on a silica gel ISCO cartridge with elution at 5 to 15% Et2O/hexane

출처 및 근거

ORD 기록
ord-e92e0028a5ca46a69992f6a78517ec20
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404896B2

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