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Hexane → (9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane

HRID 458493
Notes
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Reaction equation

HRID 458493 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=2[CH:3]=1.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33].CCCCCC>CCN(CC)CC.[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:23]([C:5]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]2[CH:3]=[C:2]([C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 8058HexaneHCID 66111TrimethylsilylacetyleneHCID 129646932-Bromo-9,9-di-n-octylfluorene2×

Product 1

HCID 18442167(9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilaneYield 86%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalyst
HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 8471TriethylamineSolvent

Procedure

To an ice-cold mixture of 2-bromo-9,9-dioctylfluorene (11.47 g, 24.4 mmol) in 100 mL Et3N was added copper (I) iodide (31.0 mg, 0.163 mmol), palladium (II) acetate (29.7 mg, 0.132 mmol) and triphenylphosphine (90.8 mg, 0.346 mmol). Trimethylsilyl acetylene (3.0 g, 30.5 mmol) was then added and the mixture stirred for 30 minutes followed by a further 30 minutes while warming to room temperature. The reaction mixture was next refluxed for 20 hours and then allowed to cool to room temperature. Thin layer chromatography (hexane as the mobile phase) showed the reaction to be complete and the formation of a reaction product with Rf value less than that of 2-bromo-9,9-dioctylfluorene. Petroleum ether was added to the reaction mixture and the insolubles filtered off. The filtrate was evaporated to dryness and the residual oil taken up in petroleum ether and washed successively with HCl (10%), NaHCO3 solution and water. Drying over magnesium sulfate and evaporation gave oil characterized as (9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane (10.2 g, 86% yield).

Workup

  1. waitfollowed by a further 30 minutes
  2. temperatureThe reaction mixture was next refluxed for 20 hours
  3. temperatureto cool to room temperature
  4. customthe reaction
  5. filtrationthe insolubles filtered off
  6. customThe filtrate was evaporated to dryness
  7. washwashed successively with HCl (10%), NaHCO3 solution and water
  8. dry with materialDrying over magnesium sulfate and evaporation
  9. customgave oil

Sources & evidence

ORD record
ord-5e2562b52e66439cbd6ed123e8fb6c3c
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07192657B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes