N-Methyl-m-anisidine → N-methyl-3-methoxyanilinochlorophenylborane

HRID 1451705Notes

Reaction equation

HRID 1451705 reaction equation
Cl[B:2]([Cl:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1>ClCCCl>[CH3:10][N:11]([B:2]([Cl:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

4

Reactant 2

HCID 84349N-Methyl-m-anisidineHCID 136678Borane, dichlorophenyl-

Product 1

HCID 15208609N-methyl-3-methoxyanilinochlorophenylborane

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-methyl-3-methoxyanilinochlorophenylborane was prepared by adding dichlorophenylborane (100 mmol) to a solution of N-methy-3-methoxyaniline (100 mmol) in 1,2-dichloroethane (100 mL) at 0° C. The resulting mixture was refluxed for 2 h under a rapid stream of nitrogen to remove the HCl formed. The mixture was cooled to give a 0.8 M cloudy solution of the title compound which could be stored at 0°C. for more than 6 weeks without deterioration.

Workup

  1. customN-methyl-3-methoxyanilinochlorophenylborane was prepared
  2. temperatureThe resulting mixture was refluxed for 2 h under a rapid stream of nitrogen
  3. customto remove the HCl
  4. customformed
  5. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-b7e1e0ee52c146258d95ef6fcb489d46
Source dataset
uspto-grants-1997_02
Patent number
US05605906

Reaction notes

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