Tris(1,1-dimethylethyl)phosphine → HCID 66797973, compound

HRID 2275957Notes

Reaction equation

HRID 2275957 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][C:23]1([CH3:43])[C:35]2[CH:34]=[C:33]3[NH:36][C:37]4[C:42]([C:32]3=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:41]N=[CH:39][CH:38]=4.[C:44](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]>[CH3:22][C:23]1([CH3:43])[C:35]2=[CH:34][C:33]3[N:36]([C:2]4[CH:3]=[C:4]([C:8]5[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([C:16]6[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=6)=[O:15])[CH:9]=5)[CH:5]=[CH:6][CH:7]=4)[C:37]4[C:42]([C:32]=3[CH:31]=[C:30]2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:41][CH:44]=[CH:39][CH:38]=4

Participants

6

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 66797721HCID 66797721, compoundHCID 66797983HCID 66797983, compound

Product 1

HCID 66797973HCID 66797973, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

15.8 g (47 mmol) of (3′-bromobiphenyl-3-yl)phenylmethanone, 13.36 g (47 mmol) of 10,10-dimethyl-10,12-dihydro-3,12-diazaindeno[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 150 ml of water and subsequently evaporated to dryness. The residue is extracted with hot toluene, recrystallised three times from toluene and finally sublimed in a high vacuum, giving 14.2 g (26.3 mmol), corresponding to 56% 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 150 ml of water
  6. customsubsequently evaporated to dryness
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised three times from toluene
  9. customgiving 14.2 g (26.3 mmol)

Sources & evidence

ORD record
ord-5398a7b55cb74ec5a9150d611ae0bca2
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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