4-Fluoro-2-nitro-1-phenoxybenzene → 5-Fluoro-2-phenoxyaniline

HRID 1930193Notes

Reaction equation

HRID 1930193 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([N+:8]([O-])=O)[CH:7]=1>CO.O=[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH:7]=1)[NH2:8]

Participants

4

Reactant 1

HCID 113792824-Fluoro-2-nitro-1-phenoxybenzene

Product 1

HCID 196271325-Fluoro-2-phenoxyanilineYield 97%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-fluoro-2-phenoxynitrobenzene 2 (15.2 g, 65 mmol) and PtO2 (131 mg) in MeOH (65 mL) was stirred at 50° C. for 5 hours under a hydrogen atmosphere. The mixture was filtered through celite. The filtrate was evaporated to dryness to yield 5-fluoro-2-phenoxyaniline 3 as brown oil (12.7 g, 97%): 1H-NMR (300 MHz, CDCl3) δ 3.88 (br s, 2H), 6.40 (ddd, J=8.6, 8.6, 3.1 Hz, 1H), 6.53(dd, J=9.9, 3.1 Hz, 1H), 6.84 (dd, J=8.6, 5.5 Hz, 1H), 6.86-7.13 (m, 3H), 7.21-7.40 (m, 2H); MS (GC) m/z 203(M., 100%). The product was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d4da59bec54543edabed3bb7e908f7c9
Source dataset
uspto-grants-2012_05
Patent number
US08188116B2

Reaction notes

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