Hydrochloric Acid → Ethyl 4-bromo-2-(trifluoromethyl)phenylcarbamate

HRID 495629Notes

Reaction equation

HRID 495629 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15].O.Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:15])[O:16][CH2:17][CH3:18])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10928Ethyl chloroformate2×HCID 679604-Bromo-2-(trifluoromethyl)aniline

Product 1

HCID 22327384Ethyl 4-bromo-2-(trifluoromethyl)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After to a solution of 4-bromo-2-trifluoromethylaniline (2.805 ml) in pyridine (15 ml) was added dropwise ethyl chloroformate (2.130 ml) during 15 minutes in an ice bath, the reaction mixture was stirred for 40 minutes. Then, to the solution was added dropwise ethyl chloroformate (1.000 ml) during 5 minutes in an ice bath again. The reaction mixture was stirred for 1 hour. After to the reaction solution was added water, 1N hydrochloric acid 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 to give the title compound (6.4509 g, quantitative yield).

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, saturated brine, saturated aqueous sodium bicarbonate solution
  5. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec0c2065dcb6478aa31febc2ea5d274c
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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