Benzyl Bromide → 2-Chloro-5-(phenylmethoxy)benzenamine

HRID 578771Notes

Reaction equation

HRID 578771 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.C(OCC)C>[CH2:18]([O:8][C:5]1[CH:4]=[C:3]([C:2]([Cl:1])=[CH:7][CH:6]=1)[NH2:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 206493762-Chloro-5-(phenylmethoxy)benzenamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Chloro-3-nitrophenol (0.13 g) was dissolved in N,N-dimethylformamide (3 mL). To the solution were added potassium carbonate (0.31 g) and benzyl bromide (0.14 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with diethyl ether, and the resulting mixture was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in tetrahydrofuran (3 mL). To the solution were added methanol (3 mL), nickel(II) bromide (8 mg) and sodium borohydride (85 mg) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. Then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.15 g).

Workup

  1. washthe resulting mixture was washed with water and brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in tetrahydrofuran (3 mL)
  5. additionTo the solution were added methanol (3 mL), nickel(II) bromide (8 mg) and sodium borohydride (85 mg) under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred at the same temperature for 30 minutes
  8. stirringThen the mixture was stirred at room temperature for 30 minutes
  9. additionThe reaction mixture was diluted with ethyl acetate
  10. washthe resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f55622d2f00a42e2b791f956a7f8379a
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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