Bromobenzene → HCID 59357764, compound

HRID 75072Notes

Reaction equation

HRID 75072 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]=[C:10]([F:20])[C:8]=2[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[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:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=[C:10]([F:20])[C:8]=2[NH:9][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 5360545SodiumHCID 59357643HCID 59357643, compound

Product 1

HCID 59357764HCID 59357764, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

2,4-diphenyl-6-fluoroaniline (12 mmol), bromobenzene (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-6-fluoro-N-phenylbenzenamine (2.5 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-d5ac651d62894259b91c0489bef21596
Source dataset
uspto-grants-2014_09
Patent number
US08835020B2

Reaction notes

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