Benzyl Bromide → 2-Benzyloxy-6-nitroaniline

HRID 1818002Notes

Reaction equation

HRID 1818002 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][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.O>[CH2:12]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 37837412-Benzyloxy-6-nitroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-3-nitro-phenol (1.54 g, 0.01 mol), benzyl bromide (1.71 g, 0.01 mol) and K2CO3 (1.54 g, 0.011 mol) in DMF (5.0 mL) was stirred at room temperature. After 20 h, reaction mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL×3). Combined organic layers were washed with 2N NaOH (20 mL×3), water (100 mL), brine (100 mL), dried over anhydrous sodium sulfate and concentrated to afford 2-Benzyloxy-6-nitro-phenylamine, I-107 (2.01 g).

Workup

  1. customreaction mixture
  2. extractionextracted with EtOAc (100 mL×3)
  3. washCombined organic layers were washed with 2N NaOH (20 mL×3), water (100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c683b08fc5054cff8aa0f249c122026a
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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