3,4-dihydro-2H-pyran → 2-(4-bromo-3-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran

HRID 1020795노트

반응식

HRID 1020795 반응식
[Br:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([OH:10])=[CH:4][C:3]=1[F:11].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>ClCCl.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[Br:1][C:2]1[C:7]([CH2:8][O:9][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[CH:6][C:5]([O:10][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:4][C:3]=1[F:11]

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 667266582-Bromo-3-fluoro-5-hydroxybenzyl alcohol

생성물 1

HCID 667261942-(4-bromo-3-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran수율 92.1%

시약·촉매·용매 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-bromo-3-fluoro-5-(hydroxymethyl)phenol (5.64 g, 25.5 mmol), 3,4-dihydro-2H-pyran (5.8 mL, 64 mmol), and dl-camphorsulfonic acid (118 mg, 2 mol %) in dichloromethane (150 mL) was stirred at room temperature for overnight. The mixture was washed with saturated aqueous sodium bicarbonate and brine, and dried on anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (9:1 hexane/ethyl acetate) to give 2-(4-bromo-3-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran (9.14 g, 92%).

후처리

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (9:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-e0016dcd3b804ad5947d97beee685d82
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716478B2

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