Potassium Carbonate → Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate

HRID 495631Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30]Br>CN(C)C=O.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[C:5]([N:12]([CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[Cl:27])[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate (475.5 mg) was dissolved in N,N-dimethylformamide (10 ml), and to the solution were added potassium carbonate (220.9 mg) and 2-chlorobenzyl bromide (0.207 ml). Then the mixture was heated at 50° C. and stirred for 1 hour. After allowing to cool, to the reaction mixture was added saturated brine, 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 to give the title compound (757.2 mg, quantitative yield).

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

Sources & evidence

ORD record: ord-bb5af297003b4455b371b31cd1981fe5
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939887B2

Reaction notes

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