Tris(1,1-dimethylethyl)phosphine → 9-(4-[Benzoxazol-2-yl)phenyl]-3-phenyl-9H-carbazole

HRID 1028869Notes

Reaction equation

HRID 1028869 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:17]1([C:23]2[CH:24]=[CH:25][C:26]3[NH:27][C:28]4[C:33]([C:34]=3[CH:35]=2)=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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].C1(C)C=CC=CC=1.CCCCCC>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([N:27]2[C:26]3[CH:25]=[CH:24][C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 128467152-(4-Bromophenyl)benzo(d)oxazoleHCID 134974733-Phenyl-9H-carbazoleHCID 23676156Sodium t-butoxide

Product 1

HCID 582818049-(4-[Benzoxazol-2-yl)phenyl]-3-phenyl-9H-carbazole

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 100 mL three-neck flask were put 1.0 g (3.7 mmol) of 2-(4-bromophenyl)benzoxazole, 0.89 g (3.7 mmol) of 3-phenyl-9H-carbazole, and 0.77 g (8.0 mmol) of sodium tert-butoxide. The atmosphere in the flask was replaced with nitrogen. To this mixture were added 30 mL of toluene and 0.10 mL of a 10% hexane solution of tri(tert-butyl)phosphine. This mixture was degassed by reducing the pressure in the flask by using an aspirator. After that, the atmosphere in the flask was replaced with nitrogen. To this mixture was added 0.058 g (0.10 mmol) of bis (dibenzylideneacetone)palladium(0), followed by stirring under a nitrogen stream at 80° C. for 15 hours. After that, toluene was added to this mixture, and this suspension was washed with a saturated aqueous sodium carbonate solution and saturated brine in that order. After that, magnesium sulfate was added to the organic layer to dry it. Next, this mixture was suction filtered, whereby a filtrate was obtained.

Workup

  1. customIn a 100 mL three-neck flask were put
  2. customThis mixture was degassed
  3. washthis suspension was washed with a saturated aqueous sodium carbonate solution and saturated brine in that order
  4. additionAfter that, magnesium sulfate was added to the organic layer
  5. customto dry it
  6. filtrationfiltered
  7. customwhereby a filtrate was obtained

Sources & evidence

ORD record
ord-40635b08bf274ff2baea59ea06a827b8
Source dataset
uspto-grants-2014_05
Patent number
US08735597B2

Reaction notes

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