2-(Benzyloxy)-1,3-difluoro-5-nitrobenzene → 4-Amino-2,6-difluorophenol

HRID 450435Notes

Reaction equation

HRID 450435 reaction equation
C([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[F:19])C1C=CC=CC=1>C(O)C.[Pd]>[NH2:16][C:12]1[CH:13]=[C:14]([F:15])[C:9]([OH:8])=[C:10]([F:19])[CH:11]=1

Participants

4

Reactant 1

HCID 231303422-(Benzyloxy)-1,3-difluoro-5-nitrobenzene

Product 1

HCID 27787644-Amino-2,6-difluorophenolYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(benzyloxy)-1,3-difluoro-5-nitrobenzene (5.3 g, 20 mol) in ethanol (100 mL) was added 10% palladium on activated carbon (1.5 g). The mixture was hydrogenated (1 atm) at RT overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give 4-amino-2,6-difluorophenol (2.9 g, 95% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (brs, 1H), 6.19 (d, J=10.8 Hz, 2H), 5.01 (s, 2H).

Workup

  1. customat RT
  2. customovernight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cbf0af702baf4d6fab68af48a48a72ca
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

Loading…