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Acetonitrile → [2-(2,5-Difluorophenyl)-6-hydroxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

HRID 1513955
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인쇄 미리보기

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HRID 1513955 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22].B(Br)(Br)Br.C(#N)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57552548[2-(2,5-Difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

생성물 1

HCID 67004531[2-(2,5-Difluorophenyl)-6-hydroxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone수율 87.9%

시약·촉매·용매

1
HCID 6344Dichloromethane용매

실험 절차

Convert [2-(2,5-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (1.8 g, 3.5 mmol) to the hydrochloride salt and dissolve it in 300 mL methylene chloride. Chill the mixture in ice and slowly add boron tribromide (5.0 mL, 53.0 mmol) with swirling. Allow the mixture to come to room temperature and stir for two hours. Add to this mixture acetonitrile (15 mL) slowly and with stirring which produces an orange precipitate. Pour the mixture into saturated sodium bicarbonate with stirring, separate the organic layer and dry with molecular sieves to give 1.5 g of the title compound (86%).

후처리

  1. temperatureChill the mixture in ice
  2. customto come to room temperature
  3. stirringwith stirring which
  4. customproduces an orange precipitate
  5. stirringwith stirring
  6. customseparate the organic layer
  7. customdry with molecular sieves

출처 및 근거

ORD 기록
ord-60d81fabc8e84d749c6ba13d52f7e4d8
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217032B2

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