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

HRID 406395ノート

反応式

HRID 406395 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 611662Methyl 3-bromo-4-methoxybenzoateHCID 178418443HCID 178418443、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ffa595b7212d474fb047107de8a57166
出典データセット
uspto-grants-2014_06
特許番号
US08754100B2

反応ノート

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