(3-Bromo-5-nitrophenyl)methanol → (3-Amino-5-bromophenyl)methanol

HRID 391429

Reaction equation

HRID 391429 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>CO.[Pt](=O)=O>[NH2:8][C:6]1[CH:5]=[C:4]([CH2:11][OH:12])[CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

4

Reactant 1

HCID 14866972(3-Bromo-5-nitrophenyl)methanol

Product 1

HCID 58993589(3-Amino-5-bromophenyl)methanol

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

(3-Bromo-5-nitrophenyl)methanol (3.9 g, 16.8 mmol) in methanol (35 mL) was flushed with nitrogen, and treated with platinum (IV) oxide (390 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen for 1 h. The reaction was flushed with nitrogen, filtered through celite, and concentrated to afford 3.1 g (94%). 1H-NMR (CDCl3, 300 MHz) δ 6.95 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 4.61 (s, 2H). Mass spec.: 203.96 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto afford 3.1 g (94%)

Sources & evidence

ORD record
ord-e4f63e5b3b20495b971be59e1fb5bc9b
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

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