1-Bromo-2-fluorobenzene → 2,4-diphenyl-N-2-fluorophenylbenzenamine

HRID 75074

Reaction equation

HRID 75074 reaction equation
[C:1]1([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27].[Na]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[NH:9][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 612591-Bromo-2-fluorobenzeneHCID 5360545SodiumHCID 123166382,4-Diphenylaniline

Product 1

HCID 593575922,4-diphenyl-N-2-fluorophenylbenzenamineYield 61.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

2,4-diphenylaniline (12 mmol), 1-bromo-2-fluorobenzene (10 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.15 mmol), (±)-2,2′-bis(diphenylphosphine)-1,1′-binaphthalene (0.3 mmol) and sodium tert-butoxie (14 mmol) are put in a two-neck round-bottom flask and dissolved in toluene (30 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, toluene is removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering with dichloromethane and petroleum ether, 2,4-diphenyl-N-2-fluorophenylbenzenamine (2.1 g) is yielded.

Workup

  1. customis removed
  2. extractionThe reaction mixture is extracted with dichloromethane and water
  3. distillationbeing distilled under reduced pressure
  4. filtrationThe resulting residence is filtered by silica gel column
  5. distillationdistilled under reduced pressure again
  6. customNext, by re-crystallizing
  7. filtrationfiltering with dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-bc715d726b214670b8b515c9efd95368
Source dataset
uspto-grants-2014_09
Patent number
US08835020B2

Linked notes

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