Tetrahydrofuran → 9-(4'-Carbazol-9-ylbiphenyl-4-yl)-2-(4-vinylphenyl)-9H-carbazole

HRID 1628373Notes

Reaction equation

HRID 1628373 reaction equation
[CH2:1]1COCC1.[CH:6]1[C:18]2[N:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([N:31]5[C:43]6[CH:42]=[C:41]([C:44]7[CH:51]=[CH:50][C:47]([CH:48]=O)=[CH:46][CH:45]=7)[CH:40]=[CH:39][C:38]=6[C:37]6[C:32]5=[CH:33][CH:34]=[CH:35][CH:36]=6)=[CH:27][CH:26]=4)=[CH:21][CH:20]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.C(C1C=CC(C2N=C(C3C=CC(C(C)(C)C)=CC=3)N=C(C3C=CC(C4C=CC(C=C)=CC=4)=CC=3)N=2)=CC=1)(C)(C)C.BrC1C=C(Br)C=C(Br)C=1I>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl>[CH:6]1[C:18]2[N:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([N:31]5[C:43]6[CH:42]=[C:41]([C:44]7[CH:51]=[CH:50][C:47]([CH:48]=[CH2:1])=[CH:46][CH:45]=7)[CH:40]=[CH:39][C:38]=6[C:37]6[C:32]5=[CH:33][CH:34]=[CH:35][CH:36]=6)=[CH:27][CH:26]=4)=[CH:21][CH:20]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 1408441-Iodo-2,4,6-tribromobenzeneHCID 594397822,4-Bis-(4-tert-butylphenyl)-6-(4'-vinylbiphenyl-4-yl)-1,3,5-triazineHCID 866917674-[9-(4'-Carbazol-9-ylbiphenyl-4-yl)-9H-carbazol-2-yl]benzaldehyde

Product 1

HCID 682786649-(4'-Carbazol-9-ylbiphenyl-4-yl)-2-(4-vinylphenyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.86 g (0.00767 mol) of potassium tert-butoxylate and 2.55 g (0.00714 mol) of methyltriphenylphosphonium bromide are initially introduced. The apparatus is cooled to 0° C., and the solids are dissolved using 15 ml of THF (abs.). The mixture is stirred for 30 min, while, in a second apparatus, 2.31 g (0.0039 mol) of 4-[9-(4′-carbazol-9-ylbiphenyl-4-yl)-9H-carbazol-2-yl]benzaldehyde is weighed out and dissolved using 25 ml of THF. At 0° C., solution 2 is added to solution 1 and stirred for a further 1.5 h. The mixture is taken up in CH2Cl2 and washed by shaking three times with water. The combined organic phases are dried over magnesium sulfate, filtered off and evaporated to dryness. Column chromatography with toluene give 2.1 g (93%) of clean substance.

Workup

  1. dissolutionthe solids are dissolved
  2. dissolutiondissolved
  3. stirringstirred for a further 1.5 h
  4. washwashed
  5. stirringby shaking three times with water
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered off
  8. customevaporated to dryness
  9. customColumn chromatography with toluene give 2.1 g (93%) of clean substance

Sources & evidence

ORD record
ord-27df9e9903fa48979ff0ad88cab22140
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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