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

HRID 7055
Notes
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Reaction equation

HRID 7055 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-64dd8aed2e704a5db3218f40da5b57c0
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084176B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes