(2-Fluoro-4-nitrophenyl)methanol → (4-Amino-2-fluorophenyl)methanol

HRID 1842879Notes

Reaction equation

HRID 1842879 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][OH:12]>CCOC(C)=O.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][OH:12])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 17981733(2-Fluoro-4-nitrophenyl)methanol

Product 1

HCID 45116731(4-Amino-2-fluorophenyl)methanolYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2-fluoro-4-nitrophenyl)methanol (3.0 g, 1.0 eq.) in EtOAc (30 mL) was added 10% Pd—C and the reaction mixture was stirred under H2 gas balloon at RT for 6 h. The reaction mixture was passed through a celite pad and the solvent evaporated. The residue was purified by neutral alumina column using PE/EtOAc (3:2) as eluent to get (4-amino-2-fluorophenyl)methanol (1.1 g, 48%) as a solid; TLC system: EtOAc/PE (1:1), Rf: 0.3).

Workup

  1. customthe solvent evaporated
  2. customThe residue was purified by neutral alumina column

Sources & evidence

ORD record
ord-22043011805e4ce7a757dcefcfec0f29
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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