tert-Butylphosphine → Tris[3-(carbazol-9-yl)phenyl]amine

HRID 555218

Reaction equation

HRID 555218 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N:27]5[C:39]6[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=6[C:33]6[C:28]5=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:22]=4)[CH:17]=[CH:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:41]1[CH:42]=[C:43]([N:47]2[C:59]3[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=3[C:53]3[C:48]2=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:44]=[CH:45][CH:46]=1.CC(C)([O-])C.[Na+].C(P)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:10]1[C:11]2[N:12]([C:14]3[CH:15]=[C:16]([N:20]([C:45]4[CH:46]=[CH:41][CH:42]=[C:43]([N:47]5[C:48]6[CH:49]=[CH:50][CH:51]=[CH:52][C:53]=6[C:54]6[C:59]5=[CH:58][CH:57]=[CH:56][CH:55]=6)[CH:44]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N:27]5[C:39]6[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=6[C:33]6[C:28]5=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:22]=4)[CH:17]=[CH:18][CH:19]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 123165tert-ButylphosphineHCID 20648014Bis[3-(carbazol-9-yl)phenyl]amineHCID 23676156Sodium t-butoxideHCID 669877889-(3-iodophenyl)-9H-carbazole

Product 1

HCID 57578466Tris[3-(carbazol-9-yl)phenyl]amineYield 56%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

5.5 g of bis[3-(carbazol-9-yl)phenyl]amine, 4.9 g of 9-(3-iodophenyl)carbazole, 2.1 g of sodium tert-butoxide, 0.1 g of palladium acetate, and 50 ml of anhydrous toluene were added in a flask under a nitrogen atmosphere. At an inner temperature of 71° C., 0.4 g of tert-butylphosphine was added by using a syringe. After 10 hours of reaction at 100° C., 300 ml of toluene was added to extract the objective substance, followed by filtration. The filtrate was concentrated to dryness to obtain a crude product. The dried crude product was purified by column chromatography to obtain 5.3 g (yield 56%) of mTCTA (Compound 2). The product was identified by 1H-NMR analysis (see FIG. 1). The following 36 hydrogen atoms were detected upon 1H-NMR (CDCl3) analysis. δ (ppm): 8.083-8.130 ppm (6H), 7.468-7.565 ppm (6H), 7.128-7.390 ppm (24H).

Workup

  1. customAfter 10 hours of reaction at 100° C.
  2. extractionto extract the objective substance
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated to dryness
  5. customto obtain a crude product
  6. customThe dried crude product
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d1b869f12e244964a958a364acbb6fb7
Source dataset
uspto-grants-2011_11
Patent number
US08053092B2

Linked notes

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