Water → HCID 60755716, compound

HRID 1754930Notes

Reaction equation

HRID 1754930 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Br:6][C:7]1[CH:8]=[C:9]([NH2:14])[CH:10]=[CH:11][C:12]=1[CH3:13].O>N1C=CC=CC=1>[CH3:5][O:4][C:2](=[O:3])[NH:14][C:9]1[CH:10]=[CH:11][C:12]([CH3:13])=[C:7]([Br:6])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6586Methyl chloroformateHCID 82187Benzenamine, 3-bromo-4-methyl-

Product 1

HCID 60755716HCID 60755716, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl chloroformate (0.202 ml, 2.62 mmol) was added to a solution of 3-bromo-4-methyl-phenylamine (243 mg, 1.31 mmol) in pyridine (2 ml), and the mixture was stirred at room temperature overnight. H2O was added to the reaction mixture, followed by extraction with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-hexane/AcOEt) to give (3-bromo-4-methyl-phenyl)-carbamic acid methyl ester (288 mg, 90%).

Workup

  1. extractionfollowed by extraction with AcOEt (×2)
  2. washsequentially washed with H2O and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (n-hexane/AcOEt)

Sources & evidence

ORD record
ord-02777fb17c8c42489e34d370a2029d50
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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