1-Nitro-4-(2,2,3,3-tetrafluoropropoxy)benzene → 4-(2,2,3,3-Tetrafluoropropoxy)aniline

HRID 450088Notes

Reaction equation

HRID 450088 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[F:16][C:12]([F:17])([CH:13]([F:14])[F:15])[CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 196147161-Nitro-4-(2,2,3,3-tetrafluoropropoxy)benzene

Product 1

HCID 187663254-(2,2,3,3-Tetrafluoropropoxy)anilineYield 56.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

Iron powder (1.3 g, 23.2 mol) was added to a solution of 1-nitro-4-(2,2,3,3-tetrafluoro-propoxy)-benzene (600 mg, 2.4 mmol) in acetic acid (4 ml) and heated at 50-60° C. for 1 hr. The reaction mixture was filtered hot over celite and washed with ethyl acetate. The filtrate was washed with water, 5% sodium hydroxide solution, brine and then dried over anhydrous sodium sulfate. The filtrate was evaporated to dryness to yield 4-(2,2,3,3-tetrafluoro-propoxy)-phenylamine (300 mg, 56.7%) as solid.

Workup

  1. filtrationThe reaction mixture was filtered hot over celite
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with water, 5% sodium hydroxide solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-81d4ed43685a45da87718cfb1fa0407c
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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