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Ethanol → 1-(4,4-Dimethylcyclohex-1-enyl)-2-nitrobenzene

HRID 2218785
Notes
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Reaction equation

HRID 2218785 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)([O-:3])=[O:2].C(O)C.[CH3:16][C:17]1([CH3:31])[CH2:22][CH2:21][C:20](OS(C(F)(F)F)(=O)=O)=[CH:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:16][C:17]1([CH3:31])[CH2:22][CH2:21][C:20]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:19][CH2:18]1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2773548(2-Nitrophenyl)boronic acidHCID 134116684,4-Dimethylcyclohex-1-ene-1-triflate

Product 1

HCID 231420031-(4,4-Dimethylcyclohex-1-enyl)-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-nitrophenylboronic acid (14.2 g, 85.19 mmol) in toluene (250 mL)-ethanol (125 mL) were added trifluoromethanesulfonic acid 4,4-dimethylcyclohex-1-enyl ester (20 g, 77.44 mmol) prepared in Example (1a), tetrakis(triphenylphosphine)palladium(0) (4.5 g, 3.87 mmol) and 2N aqueous sodium carbonate (128 mL, 256 mmol). The mixture was stirred at an external temperature of 100° C. for 1 hour and 45 minutes under a nitrogen atmosphere.

Sources & evidence

ORD record
ord-deef0f1de637471b9d956ffa49bc8083
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07410971B2

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes