Potassium Carbonate → 4-chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline

HRID 1271752Notes

Reaction equation

HRID 1271752 reaction equation
[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>O1CCCC1>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH:6][C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 141574954-Chloro-2-fluoro-5-methylaniline

Product 1

HCID 186156474-chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-fluoro-5-methylaniline (5 g, 31.4 mmol) was dissolved in tetrahydrofuran (100 ml) and potassium carbonate (6.0 g, 37.7 mmol) and phenyl chloroformate (5.9 g, 37.7 mmol) were added. Solution was refluxed for 3 hr and the solvent was removed under reduced pressure. Product was purified by column chromatography on silica gel (eluent, methylene chloride:hexane, 6:4; 7.15 g).

Workup

  1. temperatureSolution was refluxed for 3 hr
  2. customthe solvent was removed under reduced pressure
  3. customProduct was purified by column chromatography on silica gel (eluent, methylene chloride:hexane, 6:4; 7.15 g)

Sources & evidence

ORD record
ord-2b4200f0b6254408b78a1fb33f92e7be
Source dataset
uspto-grants-2007_04
Patent number
USRE039590E1

Reaction notes

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