Water → 1-(3-Bromo-4-methoxyphenyl)cyclopropanol

HRID 406395노트

반응식

HRID 406395 반응식
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11]C)=O.C(OCC)(=O)C.O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:5][C:6]1[CH:7]=[C:8]([C:9]2([OH:11])[CH2:2][CH2:1]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 611662Methyl 3-bromo-4-methoxybenzoateHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 626698761-(3-Bromo-4-methoxyphenyl)cyclopropanol

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

Ethylmagnesium bromide (3M solution in diethyl ether, 54.4 ml) was added at room temperature to a solution of methyl 3-bromo-4-methoxybenzoate (CAS No. 35450-37-4, 10 g) and titanium (IV) isopropoxide (23.9 ml) in THF (100 ml). The reaction mixture was stirred at room temperature overnight. Ethyl acetate and water were added to the reaction mixture and the precipitate was removed through Celite. The organic layer was separated, washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (7.77 g).

후처리

  1. customthe precipitate was removed through Celite
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ffa595b7212d474fb047107de8a57166
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754100B2

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