HCID 19841466, compound → 4-Amino-2-bromo-3,6-dimethylphenol

HRID 1638753Notes

Reaction equation

HRID 1638753 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[C:4]([CH3:12])[C:3]=1[OH:13]>C(OCC)(=O)C>[NH2:9][C:6]1[CH:5]=[C:4]([CH3:12])[C:3]([OH:13])=[C:2]([Br:1])[C:7]=1[CH3:8]

Participants

3

Reactant 1

HCID 19841466HCID 19841466, compound

Product 1

HCID 198414584-Amino-2-bromo-3,6-dimethylphenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a Parr bottle was charged 2-bromo-3,6-dimethyl-4-nitrophenol (13.6 grams, 55.3 mmol) prepared in Part A and ethyl acetate (50 milliliters). The reaction vessel was purged with nitrogen and 5% platinum on carbon (1.36 grams) was added immediately following the purge. Hydrogenation was carried out on a rocking Parr hydrogenator for 1.5 hours at 40-50 psi hydrogen and room temperature. The reaction mixture was filtered through celite and concentrated under reduced pressure to give 4-amino-2-bromo-3,6-dimethylphenol as a brown solid in quantitative yield. H'-NMR (CDCl3 -DMSO-d6), 6.40 (S, 1H), 2.17 (brS, 6H).

Workup

  1. customThe reaction vessel was purged with nitrogen and 5% platinum on carbon (1.36 grams)
  2. additionwas added immediately
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe2305859287493b9029d0a8bc72fb6e
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

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