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

HRID 2093284Notes

Reaction equation

HRID 2093284 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[Cl:16]>[Pt].C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[Cl:16]

Participants

4

Reactant 1

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

Product 1

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Under nitrogen, a Parr Shaker flask was charged with Pt/C 5% (135 mg) and ethanol (180 mL) and 4-(3-fluorobenzyloxy)-3-chloro nitrobenzene (13.5 g) was added. The reaction vessel was placed on a Parr Shaker Apparatus under 25 psi of H2 for 50 minutes. The catalyst was then removed by filtration through Celite and the filtrate concentrated to afford a light grey solid. The filtrate was triturated with diethyl ether and the solids collected by filtration (12.05 g, ˜100% yield).

Workup

  1. additionwas added
  2. customThe catalyst was then removed by filtration through Celite
  3. concentrationthe filtrate concentrated
  4. customto afford a light grey solid
  5. customThe filtrate was triturated with diethyl ether
  6. filtrationthe solids collected by filtration (12.05 g, ˜100% yield)

Sources & evidence

ORD record
ord-1929a573b0474f5c8bc605284311d6a0
Source dataset
uspto-grants-2013_05
Patent number
US08444988B2

Reaction notes

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