Hydrochloric Acid → Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamate

HRID 495653Notes

Reaction equation

HRID 495653 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+].[F:27][C:28]([F:38])([F:37])[C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br.Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[C:5]([N:12]([CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([C:28]([F:27])([F:37])[F:38])[CH:30]=2)[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 20827743Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate

Product 1

HCID 22327411Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate (275.3 mg) and potassium carbonate (108.3 mg) in N,N-dimethylformamide (5 ml) was added 3-trifluoromethylbenzyl bromide (0.180 ml). After the mixture was stirred at room temperature for 1 hour, 1N hydrochloric acid (ca. 30 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated brine, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (35 g, hexane:ethyl acetate=20:1) to give the title compound (345.3 mg, 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, saturated brine, saturated aqueous sodium bicarbonate solution
  3. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by silica gel column (35 g, hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-63df68f00d864015bb8d070bbd6e222f
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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