2-(2-Fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol → 2-(4-Amino-2-fluorophenyl)-2-methylpropane-1,3-diol

HRID 1842965Notes

Reaction equation

HRID 1842965 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13]>C(O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]([CH3:16])([CH2:12][OH:13])[CH2:14][OH:15])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 708166542-(2-Fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol

Product 1

HCID 866721622-(4-Amino-2-fluorophenyl)-2-methylpropane-1,3-diolYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(2-fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol (100 mg, 0.34 mmol, 1.0 eq) in ethanol was added 10% Pd/C (30 mg) and the mixture was stirred under hydrogen gas balloon atmosphere for 3 h at RT. The reaction mixture was filtered through celite pad and filtrate concentrated under vacuum to get 2-(4-amino-2-fluorophenyl)-2-methylpropane-1,3-diol (65 mg, 76%; TLC system: EtOAc/PE (1:1), Rf: 0.4).

Workup

  1. filtrationThe reaction mixture was filtered through celite pad and filtrate
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-82974dfcdd2a43d6894a91142f83e444
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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