Tris(1,1-dimethylethyl)phosphine → 2,4-diphenyl-1,3,5-triazine

HRID 2275962Notes

Reaction equation

HRID 2275962 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12](C3C=CC=C(Br)C=3)[N:11]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C2=CC3NC4C(C=3C=C2C2C1=CC=CC=2)=CC=CC=4.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC1C=CC(C)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:21]1([C:10]2[N:11]=[CH:12][N:13]=[C:8]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=3)[N:9]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazoleHCID 66797926HCID 66797926, compound

Product 1

HCID 159122,4-diphenyl-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

10.9 g (23.5 mmol) of 2,4-bis(3-bromophenyl)-6-phenyl-1,3,5-triazine, 13.3 g (47 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]-fluorene and 29.2 g of Rb2CO3 are suspended in 250 ml of p-xylene. 0.95 g (4.2 mmol) of Pd(OAc)2 and 12.6 ml of a 1 M tri-tert-butylphosphine solution are added to this suspension. The reaction mixture is heated under reflux for 24 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and evaporated to dryness. The residue is extracted with hot toluene and recrystallised three times from toluene and finally sublimed in a high vacuum, giving 13.1 g (15 mmol), corresponding to 53% of theory. The purity is 99.9%.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 200 ml of water
  6. customevaporated to dryness
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised three times from toluene
  9. customgiving 13.1 g (15 mmol)

Sources & evidence

ORD record
ord-3ba186a7e8f949d8a778f0d42d32a741
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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