Cesium carbonate → 6-(4-Fluoro-2-methylphenoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63629

반응식

HRID 63629 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH3:21])[CH:15]=1.N1C=CC=CC=1CC(C)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)=[C:16]([CH3:21])[CH:15]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 959101-(Pyridin-2-yl)propan-2-oneHCID 1362954-Fluoro-2-methylphenolHCID 101050696-Bromo-1-tetralone

생성물 1

HCID 1185981606-(4-Fluoro-2-methylphenoxy)-1,2,3,4-tetrahydronaphthalen-1-one수율 95.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To a suspension of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol), 4-fluoro-2-methylphenol (1.7 g, 13.3 mmol), 1-pyridin-2-ylacetone (240 mg, 1.8 mmol) and Cs2CO3 (5.8 g, 17.8 mmol) in DMSO (40 mL) was added CuBr (127 mg, 0.9 mmol) at rt under N2. The reaction was stirred at 100° C. overnight. The reaction was cooled, diluted with water (50 mL), and extracted with EtOAc (3×50 mL). Organics were washed with water (3×50 mL) and brine (50 mL), dried (Na2SO4), and concentrated. Purification by silica gel chromatography (PE:EtOAc=30:1) gave 2.3 g (95%) of the title compound as a colorless oil. [M+H] Calc'd for C17H15FO2, 271. Found, 271.

후처리

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc (3×50 mL)
  3. washOrganics were washed with water (3×50 mL) and brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (PE:EtOAc=30:1)

출처 및 근거

ORD 기록
ord-1d69527dfb824fd28985ca2c6f39fa80
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

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