Hydrochloric Acid → Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate

HRID 495632Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1.Cl.[CH3:30][N:31](C)C=O>[C-]#N.[Zn+2].[C-]#N.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>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:12]([C:5]1[C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]([C:30]#[N:31])=[CH:3][C:4]=1[N+:26]([O-:28])=[O:27])[C:13](=[O:17])[O:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate (620.3 mg) was dissolved in N,N-dimethylformamide (30 ml), and to the solution were added zinc cyanide (302.4 mg) and tetrakis(triphenylphosphine)palladium(0) (1.116 g). The mixture was heated at 60° C. and stirred for 7 hours. After allowing to cool, to the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=3:1) to give the title compound (322.6 mg, 59%).

Workup

temperatureto cool, to the reaction mixture
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-d4498674f1fa409bba71912b1bf7b4ed
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939887B2

Reaction notes

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