Sodium Carbonate → HCID 58978754, compound

HRID 1180529Notes

Reaction equation

HRID 1180529 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:11]=3[CH:10]=2)O1.Br[C:40]1[C:45]2=[N:46][S:47][N:48]=[C:44]2[C:43](Br)=[CH:42][CH:41]=1.C([O-])([O-])=O.[Na+].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH2:30]([C:12]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:11]2[CH:10]=[C:9]([C:40]3[C:45]4=[N:46][S:47][N:48]=[C:44]4[C:43]([C:9]4[CH:21]=[CH:20][C:19]5[C:18]6[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=6)[C:12]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:11]=5[CH:10]=4)=[CH:42][CH:41]=3)[CH:21]=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 114778562-(9,9-Dioctyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 58978754HCID 58978754, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a flask was introduced 100 mL of toluene, 8.77 g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (10) (17 mmol), 2 g of 4,7-dibromo-benzo[1,2,5]thiadiazole (5) (6.8 mmole), 0.69 g of Aliquat® 336 (1.7 mmol) and 17.2 mL of aqueous 2M Na2CO3. This was N2 purged for 1 h. The flask was heated to about 80° C. and 33 mg of tetrakistriphenylphosphine palladium (0) (0.0042 mmol) then added under a nitrogen purge. The content of the flask was refluxed for 3 days. The reaction flask was allowed to cool to RT and about 50 mL water added and the organic layer separated. The aqueous layer was extracted with 50 mL toluene. The organic layers were combined and washed successively with water twice and then dried over MgSO4. Concentration gave an oil which was purified by flash chromatography (eluent: 10% CH2Cl2 in Hexane) to give 4.0 g (64% yield) of 4,7-Bis-(9,9-dioctyl-9H-fluoren-2-yl)-benzo[1,2,5]thiadiazole 16 as a green solid. Compound 16 was shown to exhibit a blue-white fluorescence (425 nm and 518 nm emissions) in dilute toluene solution when excited at 375 nm. At 0.2 mg/mL or as a spin cast thin film, this compound gave a green fluorescence (518 nm) under UV excitation.

Workup

  1. customThis was N2 purged for 1 h
  2. custompurge
  3. temperatureThe content of the flask was refluxed for 3 days
  4. temperatureto cool to RT
  5. additionabout 50 mL water added
  6. customthe organic layer separated
  7. extractionThe aqueous layer was extracted with 50 mL toluene
  8. washwashed successively with water twice
  9. dry with materialdried over MgSO4
  10. concentrationConcentration
  11. customgave an oil which
  12. customwas purified by flash chromatography (eluent: 10% CH2Cl2 in Hexane)

Sources & evidence

ORD record
ord-b833f7accd754d65971c92fdc2e8a5ef
Source dataset
uspto-grants-2007_10
Patent number
US07282275B2

Reaction notes

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