4-Bromo-3-methyl-2-nitrophenol → 2-amino-4-bromo-3-methylphenol

HRID 1912606Notes

Reaction equation

HRID 1912606 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].[H][H]>CO.[Pt]>[NH2:9][C:4]1[C:3]([CH3:12])=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

5

Reactant 2

HCID 130881794-Bromo-3-methyl-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 595785452-amino-4-bromo-3-methylphenolYield 99%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

4-Bromo-3-methyl-2-nitrophenol (10 g, 43.1 mmol) was dissolved in methanol (254 ml), purged with nitrogen and loaded with Pt/C (1.013 g, 10.13 mmol). The reaction was stirred under 60 psi of hydrogen for 5 hours. When complete, the reaction was filtered carefully on Celite™. The top was covered by more Celite™, flushed with ethyl acetate and dichloromethane and allowed to dry a bit before adding more. The organics were concentrated and 2-amino-4-bromo-3-methylphenol (8.6 g, 99%) was isolated as a brown solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.67 (d, J=9.0 Hz, 1 H), 6.93 (d, J=9.0 Hz, 1 H), 2.63 (s, 3 H); LC/MS (m/z) ES+=202 (M+1).

Workup

  1. custompurged with nitrogen
  2. filtrationWhen complete, the reaction was filtered carefully on Celite™
  3. customflushed with ethyl acetate and dichloromethane
  4. customto dry a bit
  5. additionbefore adding more
  6. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-ad1ead728875490f8f9e2e095e2ca9fd
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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