2-Bromo-1-(3-fluorobenzyloxy)-4-nitrobenzene → 3-Bromo-4-[(3-fluorophenyl)methoxy]aniline

HRID 877102Notes

Reaction equation

HRID 877102 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1>CO.[Pd]>[F:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][O:4][C:3]1[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:2]=1[Br:1]

Participants

4

Reactant 1

HCID 218748002-Bromo-1-(3-fluorobenzyloxy)-4-nitrobenzene

Product 1

HCID 218747953-Bromo-4-[(3-fluorophenyl)methoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1-((2-bromo-4-nitrophenoxy)methyl)-3-fluorobenzene (3.26 g) in methanol (50 mL) with palladium on carbon (10%, 300 mg) was hydrogenated on a Parr shaker for 24 hours at 60 psi. The mixture was filtered through Celite and all solvents were removed under reduced pressure to give a white crystalline solid, which was used without further purification. LCMS ESI(+) m/z: 297 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customall solvents were removed under reduced pressure
  3. customto give a white crystalline solid, which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-3f0080308572442d8fdb1a6b9b363c3d
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

Loading…