4-Bromo-6-fluoro-3-methyl-2-nitrophenol → 2-Amino-4-bromo-6-fluoro-3-methylphenol

HRID 1912640Notes

Reaction equation

HRID 1912640 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[C:3]=1[CH3:13]>CO.[Pt]>[NH2:10][C:4]1[C:3]([CH3:13])=[C:2]([Br:1])[CH:7]=[C:6]([F:8])[C:5]=1[OH:9]

Participants

4

Reactant 1

HCID 866757474-Bromo-6-fluoro-3-methyl-2-nitrophenol

Product 1

HCID 866757482-Amino-4-bromo-6-fluoro-3-methylphenolYield 106.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-6-fluoro-3-methyl-2-nitrophenol (0.69 g, 2.76 mmol) in methanol (10 mL) was purged with nitrogen, treated with 10% platinum on carbon (0.027 g, 0.014 mmol) and then stirred under hydrogen (50 psi) overnight. The mixture was filtered over Celite (washing with methanol and dichloromethane) and the filtrate was concentrated to afford 2-amino-4-bromo-6-fluoro-3-methylphenol (647 mg) as a light brown solid, which was used directly without further purification. 1H NMR (400 MHz, DMSO-d6) δ=6.68 (d, J=10.0 Hz, 1 H), 2.11 (s, 3 H); LC/MS (m/z) ES+=219.98 (M+1).

Workup

  1. customwas purged with nitrogen
  2. filtrationThe mixture was filtered over Celite (washing with methanol and dichloromethane)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b5a72868d02a46fab3d1a59004ac66cf
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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