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

HRID 32138

Reaction equation

HRID 32138 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

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 178418397HCID 178418397, compoundCatalystHCID 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-6e5393eb89fa4a778b152028f21849f0
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Linked notes

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