Benzyl Bromide → 4-Benzyloxy-3-chloroaniline

HRID 1666233Notes

Reaction equation

HRID 1666233 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12074Nitrofungin

Product 1

HCID 12682854-Benzyloxy-3-chloroanilineYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 250 mL flask equipped with a reflux condenser, 2-chloro-4-nitrophenol 4.65 g (26.6 mmol), benzyl bromide 2.97 mL (27.0 mmol, 1 eq), K2CO3 9.4 g (54 mmol, 2 eq) and DMF (60 mL) were added and then heated to reflux. The procedure was conducted as Example 1, the residue was purified by column chromatography to obtain the title compound as brown solid, total yield: 73%.

Workup

  1. customIn a 250 mL flask equipped with a reflux condenser
  2. temperatureheated to reflux
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8517173762084ce3836e73539789a259
Source dataset
uspto-grants-2011_10
Patent number
US08044063B2

Reaction notes

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