Water → 1-(Benzyloxy)-3-bromo-2-fluorobenzene

HRID 1879040노트

반응식

HRID 1879040 반응식
[Br:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CC(C)=O.C(OCC)(=O)C>[CH2:16]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[F:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 184012573-Bromo-2-fluorophenol

생성물 1

HCID 574388031-(Benzyloxy)-3-bromo-2-fluorobenzene수율 105.7%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-bromo-2-fluorophenol (1.8 g, 9.42 mmol) in acetone (25 ml) was added sodium carbonate (2.55 g, 20 mmol) and the mixture was stirred for 5 min. Benzylbromide (1.2 ml, 10.3 mmol) was added and the reaction mixture was heated at reflux for 20 h. Water (50 ml) and ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. The residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1) to give the title compound (2.8 g). MS m/z (rel. intensity, 70 eV) 282 (M+, 2), 280 (M+, 2), 163 (2), 161 (2), 91 (bp).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. dry with materialthe combined organic phases was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1)

출처 및 근거

ORD 기록
ord-fd67c3fdea1c4817a008e4751f724304
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314126B2

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