Sodium Hydroxide → HCID 20099591, compound

HRID 1270718Notes

Reaction equation

HRID 1270718 reaction equation
[F:1][C:2]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:3]=1[NH2:4].[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[OH-].[Na+]>C1C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1230504-Bromo-2-fluoroanilineHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 20099591HCID 20099591, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Fluoro-4-bromoaniline (10.7 g), 4-fluorophenylboronic acid (11.9 g), 60 mL of 2 N NaOH and 200 mL of benzene are combined and degassed with N2. Palladium tetrakistriphenylphosphine (4.2 g) is added and the mixture stirred at reflux temperature overnight. After cooling, the reaction is filtered through Celite and concentrated. The oily residue is purified by flash chromatography (5–10% EtOAc/hexane) to afford 2-fluoro-4-(4′-fluorophenyl)aniline as a solid.

Workup

  1. customdegassed with N2
  2. additionPalladium tetrakistriphenylphosphine (4.2 g) is added
  3. temperatureat reflux temperature overnight
  4. temperatureAfter cooling
  5. filtrationthe reaction is filtered through Celite
  6. concentrationconcentrated
  7. customThe oily residue is purified by flash chromatography (5–10% EtOAc/hexane)

Sources & evidence

ORD record
ord-f75e05981c024744876196a313b617a3
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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