4-(2-Fluoro-phenoxy)-2-nitrotoluene → 5-(2-Fluoro-phenoxy)-2-methyl-phenylamine

HRID 1727108Notes

Reaction equation

HRID 1727108 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([NH2:12])[CH:6]=1

Participants

4

Reactant 1

HCID 575666884-(2-Fluoro-phenoxy)-2-nitrotoluene

Product 1

HCID 575666905-(2-Fluoro-phenoxy)-2-methyl-phenylamineYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(2-fluoro-phenoxy)-2-nitrotoluene (15.17 g, 0,061 mol) and Pd/C (1.67 g) in ethanol (150 mL) were stirred under hydrogen atmosphere for 48 h, then the mixture was filtered through celite and the filtrate was concentrated under vacuum and purified by flash chromatography eluting with Hex:EtOAc 9:1 to afford 10.9 g of 5-(2-fluoro-phenoxy)-2-methyl-phenylamine: MS: 218 (M+H).

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. custompurified by flash chromatography
  4. washeluting with Hex

Sources & evidence

ORD record
ord-0b7f32ac9a5746db9362f56e36d918e8
Source dataset
uspto-grants-2009_02
Patent number
US07495015B2

Reaction notes

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