Ethyl Acetate → Methyl 2-(2-benzyloxyphenyl)-5-nitrobenzoate

HRID 909285

反応式

HRID 909285 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 2773253(2-(Benzyloxy)phenyl)boronic acid

生成物 1

HCID 58026868Methyl 2-(2-benzyloxyphenyl)-5-nitrobenzoate収率 65.2%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-benzyloxyphenylboronic acid (20.2 g, 88.6 mmol), methyl 2-bromo-5-nitrobenzoate (25.4 g, 97.5 mmol), cesium carbonate (57.7 g, 177 mmol) and bis(triphenylphosphine)palladium(II) dichloride (1.16 g, 1.65 mmol) was suspended in anhydrous N,N-dimethylformamide (300 mL), and then was stirred under argon atmosphere at 80° C. for 3 days. After cooling down, ethyl acetate (500 mL), diethylether (300 mL) and water (500 mL) were added thereto, and then separated. The aqueous layer was extracted with a mixture of ethyl acetate (200 mL) and diethylether (200 mL). The combined organic layer was washed with water (500 mL, twice) and saturated brine (300 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (21.0 g) as a pale yellow oil. (Yield 65%)

後処理

  1. temperatureAfter cooling down
  2. customseparated
  3. extractionThe aqueous layer was extracted with a mixture of ethyl acetate (200 mL) and diethylether (200 mL)
  4. washThe combined organic layer was washed with water (500 mL
  5. dry with materialtwice) and saturated brine (300 mL) successively, dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-2977104239f344e7ab4df5fc76f21ad5
出典データセット
uspto-grants-2011_09
特許番号
US08017775B2

関連ノート

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