4-Methoxystyrene → 4-Methoxy-1-[2-(4-methoxyphenyl)vinyl]-2-nitrobenzene

HRID 2423694Notes

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].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:20]=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-bromo-4-methoxy-2-nitrobenzene (2.3 g) in acetonitrile (20 ml) was sequentially added 4-methoxystyrene (1.5 g), N,N-diisopropylethylamine (3.9 g), 2-(di-tert-butylphosphino)biphenyl (145 mg) and palladium(II) acetate (112 mg), and the solution was stirred for 15 hours at 80° C. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (1.4 g).

Workup

extractionThe solution was extracted with ethyl acetate
washsequentially washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated in vacuo
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record: ord-b5be43d24658429c9df7d7cbef90bffa
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960412B2

Reaction notes

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