Pyridine → N-(2-bromo-5-trifluoromethylphenyl)carbamic acid ethyl ester

HRID 1371866Notes

Reaction equation

HRID 1371866 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH2:12].N1C=CC=CC=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CCOCC.O>[CH2:23]([O:22][C:20](=[O:21])[NH:12][C:3]1[CH:4]=[C:5]([C:8]([F:10])([F:11])[F:9])[CH:6]=[CH:7][C:2]=1[Br:1])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 679892-Bromo-5-(trifluoromethyl)benzenamine

Product 1

HCID 11738467N-(2-bromo-5-trifluoromethylphenyl)carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

Combine 2-bromo-5-trifluoromethylphenylamine (27.06 g, 112.74 mmol) and 200 mL of pyridine. Cool in an ice bath and add ethyl chloroformate (18.35 g, 169.11 mL, 1.5 eq). After addition was complete, allow the reaction to gradually warming to room temperature. After 18 hours, evaporate in vacuo to give a residue. Dissolve the residue in Et2O/water and transfer to a separatory funnel. Separate the layer and extract the aqueous layer with Et2O (2×300 mL), combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give N-(2-bromo-5-trifluoromethylphenyl)carbamic acid ethyl ester which may be used without further purification.

Workup

  1. temperatureCool in an ice bath
  2. additionAfter addition
  3. customthe reaction
  4. customevaporate in vacuo
  5. customto give a residue
  6. customSeparate the layer
  7. extractionextract the aqueous layer with Et2O (2×300 mL)
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo

Sources & evidence

ORD record
ord-31e7adcfa48e4010bea28fb6131bdbc7
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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