(2-Chloro-4-fluoro-5-nitrophenyl)methanol → (5-Amino-2-chloro-4-fluorophenyl)methanol

HRID 231430Notes

Reaction equation

HRID 231430 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-])=O)=[CH:6][C:3]=1[CH2:4][OH:5]>[Pt]=O.C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([NH2:11])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 1

HCID 13629752(2-Chloro-4-fluoro-5-nitrophenyl)methanol

Product 1

HCID 13629753(5-Amino-2-chloro-4-fluorophenyl)methanolYield 96.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

In a Parr hydrogenation apparatus were placed 6.5 g (0.032 mole) of 2-chloro-4-fluoro-5-nitrobenzyl alcohol, 0.3 g of platinum oxide catalyst, and 100 ml of glacial acetic acid. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration and the solvent was evaporated under reduced pressure, leaving 5.42 g of 2-chloro-4-fluoro-5-aminobenzyl alcohol as a tan solid. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. customHydrogenation required 1.5 hours after which the catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0511f10c3a69409e8dd92f0c1df21b33
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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