1-Bromo-2-nitrobenzene → Acetic acid 4-[2-(2-aminophenyl)vinyl]phenyl ester

HRID 1433940Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:32]([O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=[CH2:41])=[CH:38][CH:37]=1)(=[O:34])[CH3:33].C(N(CC)C(C)C)(C)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:41]=[CH:40][C:39]1[CH:42]=[CH:43][C:36]([O:35][C:32](=[O:34])[CH3:33])=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-bromo-2-nitrobenzene (2.0 g), palladium(II) acetate (112 mg) and 2-(di-tert-butylphosphino)biphenyl (150 mg) in acetonitrile (20 ml) were sequentially added 4-acetoxystyrene (1.7 ml) and N,N-diisopropylethylamine (5 ml) under a nitrogen atmosphere, and the solution was stirred for 3 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. Obtained by purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), acetic acid 4-[2-(2-nitrophenyl)vinyl]phenyl ester (840 mg) was used according to an analogous synthetic method to Example 57 to provide the title compound (330 mg).

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
customObtained
customby purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), acetic acid 4-[2-(2-nitrophenyl)vinyl]phenyl ester (840 mg)

Sources & evidence

ORD record: ord-35c6e337c43d460b894c0c0e6af9e9c6
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612114B2

Reaction notes

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