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

HRID 495631
Notes
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Reaction equation

HRID 495631 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 20827743Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate

Product 1

HCID 22327381Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 57417360
Sodium chloride; water
Solvent

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

  1. temperatureto cool, to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes