4-Bromo-2-fluoro-6-nitrophenol → 2-Amino-6-fluorophenol

HRID 7767Notes

Reaction equation

HRID 7767 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([OH:11])=[C:4]([F:12])[CH:3]=1>[Pd].CO>[NH2:8][C:6]1[CH:7]=[CH:2][CH:3]=[C:4]([F:12])[C:5]=1[OH:11]

Participants

4

Reactant 1

HCID 6881164-Bromo-2-fluoro-6-nitrophenol

Product 1

HCID 6435622-Amino-6-fluorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred slurry of 10% palladium on carbon (2.26 g, 2.12 mmol) in MeOH (100 mL) was added 4-bromo-2-fluoro-6-nitrophenol (5.00 g, 21.2 mmol). The reaction mixture was stirred under an H2 atmosphere until significant reduction was seen by TLC. The mixture was filtered through Celite and concentrated in vacuo. The resultant solid was triturated with hexanes and reconcentrated to remove residual MeOH and give 2-amino-6-fluorophenol as a dark gray solid. 1H NMR (DMSO-d6, 300 MHz) δ 10.86 (br s, 1H), 9.54 (br s, 2H), 7.25–7.19 (m, 1H), 7.13 (d, 1H), 6.94–6.86 (m, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe resultant solid was triturated with hexanes
  4. customto remove residual MeOH

Sources & evidence

ORD record
ord-90f5ba66db5b4dc8a2014e6adc3abaca
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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