3-Nitrophenylboronic Acid → 3-(Cyclohexen-1-yl)-1-nitrobenzene

HRID 7055

반응식

HRID 7055 반응식
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C(O[CH2:25][CH3:26])(=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:26]1([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=2)[CH2:25][CH2:8][CH2:9][CH2:4][CH:5]=1

참가 물질

7

반응물 4

HCID 16773-Nitrophenylboronic AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 433294Lithium Chloride

생성물 1

HCID 220196423-(Cyclohexen-1-yl)-1-nitrobenzene

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

The above product (1.3 g) is dissolved in ethylene glycol dimethyl ether (10 ml), and thereto are added 3-nitrophenylboronic acid (1.3 g), tetrakis(triphenylphosphine)palladium (0) (330 mg), lithium chloride (720 mg) and 2M aqueous sodium carbonate (8 ml), and the mixture is heated under reflux for 3 hours. To the mixture is added ethyl acetate, and the organic layer is washed with water, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 3-(cyclohexen-1-yl)-1-nitrobenzene (700 mg).

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. washthe organic layer is washed with water
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-64dd8aed2e704a5db3218f40da5b57c0
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084176B2

연결된 노트

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