Benzyl Bromide → 4-(Benzyloxy)-2-methyl-6-nitroaniline

HRID 1846502Notes

Reaction equation

HRID 1846502 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>CN(C=O)C>[CH2:19]([O:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[C:3]([CH3:12])[CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 669782964-Amino-3-methyl-5-nitrophenol

Product 1

HCID 669780234-(Benzyloxy)-2-methyl-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.84 g (5.00 mmol) 4-amino-3-methyl-5-nitrophenol was placed in 10 mL DMF, combined with 0.78 g (5.50 mmol) potassium carbonate and stirred for 10 min at RT. Then 0.65 mL (5.50 mmol) benzylbromide were added and the mixture was stirred for a further 30 min at RT and for 1 h at 60° C. Another 0.33 mL benzylbromide were added and the mixture was stirred for 1 h at 60° C. The reaction mixture was poured onto ice water, extracted with ethyl acetate and evaporated down i.vac. The residue was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 1M aqueous NaOH solution and extracted with ethyl acetate. The organic phase was evaporated down i.vac.

Workup

  1. stirringthe mixture was stirred for a further 30 min at RT and for 1 h at 60° C
  2. stirringthe mixture was stirred for 1 h at 60° C
  3. additionThe reaction mixture was poured onto ice water
  4. extractionextracted with ethyl acetate
  5. customevaporated down i.vac
  6. customThe residue was purified by chromatography
  7. additionThe fractions containing product
  8. customevaporated down i.vac
  9. customto leave the aqueous residue
  10. extractionextracted with ethyl acetate
  11. customThe organic phase was evaporated down i.vac

Sources & evidence

ORD record
ord-2bbad882c8064187bd54b92a49f4c1ac
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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