Tetrabutylammonium Fluoride → HCID 59469955, compound

HRID 2364928Notes

Reaction equation

HRID 2364928 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]1([Si:25]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[C:26]2[CH:27]=[CH:28][C:29]3[N:30]([Si](C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:31]4[C:36]([C:37]=3[CH:38]=2)=[CH:35][C:34]([Si:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:33][CH:32]=4)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:52]1([Si:39]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:34]2[CH:33]=[CH:32][C:31]3[NH:30][C:29]4[C:37]([C:36]=3[CH:35]=2)=[CH:38][C:26]([Si:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[CH:27][CH:28]=4)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58131120HCID 58131120, compound

Product 1

HCID 59469955HCID 59469955, compoundYield 120.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A TBAF solution (1M in THF, 4.6 ml, 4.6 mmol) is added to a solution of 3,6,9-tris-(triphenylsilyl)carbazole (8.7 g, 9.2 mmol) in CH2Cl2 (150 ml). After stirring for one hour, thin layer chromatography shows complete deprotection. The solvent is removed under reduced pressure, and the residue is heated under reflux in cyclohexane (150 ml). After cooling, the suspension is filtered. The residue is filtered through SiO2 (10:1 cyclohexane:EtOAc) to obtain the desired product (7.6 g, 97%). 1H NMR (CDCl3, 400 MHz): δ=7.4 (m, 20H), 7.6 (m, 14H), 8.18 (s, 2H), 8.20 (s, 1H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. temperaturethe residue is heated
  3. temperatureunder reflux in cyclohexane (150 ml)
  4. temperatureAfter cooling
  5. filtrationthe suspension is filtered
  6. filtrationThe residue is filtered through SiO2 (10:1 cyclohexane:EtOAc)

Sources & evidence

ORD record
ord-fc332bf6ce97423f92c044b13a18d766
Source dataset
uspto-grants-2014_04
Patent number
US08697255B2

Reaction notes

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