Acetic Acid → Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate

HRID 495630Notes

Reaction equation

HRID 495630 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:8]([C:18]([F:21])([F:20])[F:19])[CH:7]=1.C(O)(=O)C>S(=O)(=O)(O)O.C(OC(=O)C)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([C:18]([F:20])([F:21])[F:19])[C:9]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:10]([N+:1]([O-:4])=[O:2])[CH:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 22327384Ethyl 4-bromo-2-(trifluoromethyl)phenylcarbamate

Product 1

HCID 20827743Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamateYield 61%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent2×

Procedure

To acetic anhydride (10 ml) was added dropwise conc. nitric acid (d=1.42, 1.300 ml) during 10 minutes in an ice bath and added one drop of conc. sulfuric acid (96%). To this solution was added a solution of ethyl 4-bromo-2-(trifluoromethyl)phenylcarbamate in acetic anhydride (7 ml)/acetic acid (1 ml) during 30 minutes in an ice bath. After stirring for 2.5 hours, the reaction mixture was poured into ice-water, and the precipitated solid product was filtered. The resultant solid product was purified by silica gel column (120 g, hexane:ethyl acetate=15:1) to give the title compound (2.3265 g, 61%).

Workup

  1. filtrationthe precipitated solid product was filtered
  2. customThe resultant solid product was purified by silica gel column (120 g, hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-4f7ff19f59464b3289e3bc01cb8adf40
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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