4-Methoxystyrene → HCID 11579752, compound

HRID 2260942Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C[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.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C>[N+:10]([C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1/[CH:20]=[CH:19]/[C:18]1[CH:21]=[CH:22][C:15]([OH:14])=[CH:16][CH:17]=1)([O-:12])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-bromo-5-methoxynitrobenzene (5 g, 21.6 mmol) in dry acetonitrile (60 mL) were added 4-methoxystyrene (3.04 g, 22.6 mmol), N,N-diisopropylethylamine (8.36 g, 64.6 mmol), biphenyl-2-yl-di-t-butyl phosphine (385 mg, 1.3 mmol) and palladium acetate (290 mg, 1.3 mmol). The resulting mixture was heated at 80° C. overnight under N2. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, and dried over magnesium sulfate. Concentration under reduced pressure gave the crude product which was purified by column chromatography using ethyl acetate in hexane (5%-10%) to give the protected nitro-stilbene (4.4 g, 72%).

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with water, brine
dry with materialdried over magnesium sulfate
concentrationConcentration under reduced pressure
customgave the crude product which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-b6c4caea50dc447fa2b12a571fa284b2
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846915B2

Reaction notes

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