Water → 3-(3-Bromopropoxy-4-methoxyphenyl)phenylmethanone

HRID 233829노트

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HRID 233829 반응식
O[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]C=1)=O.[H-].[Na+].[Br:20][CH2:21][CH2:22][CH2:23]Br.[OH2:25].CN(C)[CH:28]=[O:29]>>[Br:20][CH2:21][CH2:22][CH2:23][O:25][C:3]1[CH:2]=[C:15]([O:16][CH3:17])[CH:14]=[CH:13][C:4]=1[C:5]1[CH:7]=[C:12]([CH:28]=[O:29])[CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 41488933-Hydroxy-4-methoxybenzophenone

생성물 1

HCID 219600893-(3-Bromopropoxy-4-methoxyphenyl)phenylmethanone

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온도
90 °C

실험 절차

A solution of 3-hydroxy-4-methoxybenzophenone (4.6 g, 20 mmol) in dimethylformamide (35 ml) was treated with sodium hydride (600 mg, 25 mmol) at 0° C. for 20 minutes, then 1,3-dibromopropane (5 g, 24.7 mmol) was added in one portion. The mixture was heated at 90° C. for 1 hour, and then stirred at room temperature for 2 hours. At the end of the reaction, the mixture was poured into water (500 ml) and extracted with ethyl acetate (400 ml). The ethyl acetate solution was washed with water, brine and dried over anhydrous MgSO4. The solvent was removed and the crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g; eluted with 3:1 hexane:dichloromethane, 1.6 1; 3:7 hexane: dichloromethane, 1.4 l). The pure product thus obtained weighed 4.67 g, (66%) as an oil. Recrystallization twice from isopropyl ether (500 ml) gave analytically pure 3-(3-bromopropoxy-4-methoxyphenyl)phenylmethanone (2.42 g), m.p.=81°-83° C.

후처리

  1. customAt the end of the reaction
  2. extractionextracted with ethyl acetate (400 ml)
  3. washThe ethyl acetate solution was washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed
  6. customthe crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g; eluted with 3:1 hexane:dichloromethane, 1.6 1; 3:7 hexane: dichloromethane, 1.4 l)
  7. customThe pure product thus obtained
  8. customRecrystallization twice from isopropyl ether (500 ml)

출처 및 근거

ORD 기록
ord-7ff801302b5942278b9e62e668186620
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593995

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