2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene → 3-Chloro-4-(3-fluorobenzyloxy)aniline

HRID 414999Notes

Reaction equation

HRID 414999 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1>CO.[Pt]>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1

Participants

4

Reactant 1

HCID 70592692-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene

Product 1

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineYield 83%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene (4.08 g, 14.5 mmol) is suspended in MeOH (50 ml) and treated wet 5% Pt/C (Degussa type, Aldrich, 1.5 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture is stirred under hydrogen atmosphere until reaction is judged complete by this-layer chromatography (approximately 2 hours). The reaction mixture is filtered through a Celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MgSO4) and concentrated to yield 3.1 g (12 mmol, 83%) of the desired product.

Workup

  1. customThe flask is flushed with hydrogen gas from a balloon
  2. customis judged complete by this-layer chromatography (approximately 2 hours)
  3. filtrationThe reaction mixture is filtered through a Celite plug
  4. customthe solvent is removed under reduced pressure
  5. dissolutionThe crude product is redissolved in DCM
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03eebdaba16a4a6185f6214c3f48ce7b
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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