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Triphenyl phosphite → 2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethan-1-ol

HRID 587188
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HRID 587188 반응식
BrC(C1C=C(Cl)C=C(Cl)C=1)[C:3]([F:6])([F:5])[F:4].Cl[C:16]1[CH:17]=[C:18]([CH:23]([OH:28])[C:24]([F:27])([F:26])[F:25])[CH:19]=[C:20](Cl)[CH:21]=1.C1C(=O)N(Br)C(=O)C1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(Cl)Cl>[F:25][C:24]([F:27])([F:26])[CH:23]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:3]([F:6])([F:5])[F:4])[CH:17]=1)[OH:28]
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참가 물질

6

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HCID 7540Triphenyl phosphiteHCID 67184N-bromobutanimideHCID 616446851-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanolHCID 866751181-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene

생성물 1

HCID 2445592,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethan-1-ol수율 40%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
25 °C

실험 절차

1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (AI1). To a stirred solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (4.0 g, 16.3 mmol) in CH2Cl2 (50 mL), were added NBS (2.9 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25° C. and was concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 100% pentane) afforded the title compound as a liquid (2.0 g, 40%): 1H NMR (400 MHz, CDCl3) δ 7.41 (s, 3H), 5.00 (m, 1H); EIMS m/z 306 ([M]+).

후처리

  1. customthe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 18 h
  4. concentrationwas concentrated under reduced pressure
  5. customPurification
  6. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 100% pentane)

출처 및 근거

ORD 기록
ord-615497d5e4d14abe91fd9b0f707625a6
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09226500B2

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