1-Bromo-4-fluoro-2-methyl-5-nitrobenzene → 5-Bromo-2-fluoro-4-methylaniline

HRID 522706

Reaction equation

HRID 522706 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1[CH3:12].[H][H]>[Ni].C(O)C>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:7]=1)[NH2:8]

Participants

5

Reactant 2

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 467391145-Bromo-2-fluoro-4-methylanilineYield 63.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Combine crude 1-bromo-4-fluoro-2-methyl-5-nitrobenzene (32.4 g, 138 mmol), ethanol (100 mL) and Raney Nickel (1.00 g, 17.04 mmol) in a shaker flask. Charge the flask with hydrogen (275 kPa) and agitate until the absorption of hydrogen ceases. De-pressurize the reaction vessel, remove the catalyst by filtration, and evaporate the filtrate to dryness. Add MTBE, then filter again and evaporate the filtrate. Stir residue in hexanes. Collect the solids by filtration, wash with cold hexanes and dry in vacuo to provide the title compound (17.8 g, 63% yield) as a dark solid. MS (m/z): 204.0 (M+1)/206.0 (M+3).

Workup

  1. customDe-pressurize the reaction vessel, remove the catalyst
  2. filtrationby filtration
  3. customevaporate the filtrate to dryness
  4. filtrationAdd MTBE, then filter again
  5. customevaporate the filtrate
  6. customCollect the solids
  7. filtrationby filtration
  8. washwash with cold hexanes
  9. customdry in vacuo

Sources & evidence

ORD record
ord-ee685ee613564d3fa6d76b9da194d191
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Linked notes

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