Potassium Phosphate, Tribasic → 1-(4,4-Diethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene

HRID 32141Notes

Reaction equation

HRID 32141 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([C:15]1([CH2:30][CH3:31])[CH2:20][CH2:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH2:16]1)[CH3:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.COCCOC>[CH2:13]([C:15]1([CH2:30][CH3:31])[CH2:20][CH2:19][C:18]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])=[CH:17][CH2:16]1)[CH3:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 792884-Bromo-3-nitroanisoleHCID 231417472-(4,4-Diethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 231418351-(4,4-Diethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-bromo-3-nitroanisole (2 g, 8.62 mmol), 2-(4,4-diethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.7 g, 10.3 mmol) prepared in Example (6c), tripotassium phosphate (2.7 g, 13.0 mmol) and 1,2-dimethoxyethane (20 mL) was stirred at room temperature under a nitrogen atmosphere, and then tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.43 mmol) was added. The mixture was then stirred at an external temperature of 80° C. for 26 hours.

Workup

  1. stirringThe mixture was then stirred at an external temperature of 80° C. for 26 hours

Sources & evidence

ORD record
ord-009770099b6b46d7991437d7227dbd95
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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