Sodium Carbonate → HCID 58961748, compound

HRID 917247Notes

Reaction equation

HRID 917247 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[CH:41]=[C:42]([C:47]2[O:48][C:49]([C:52]3[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[CH:54][CH:53]=3)=[N:50][N:51]=2)[CH:43]=[C:44](Br)[CH:45]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:22]([C:12]1([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:13]2[CH:14]=[C:15]([C:40]3[CH:41]=[C:42]([C:47]4[O:48][C:49]([C:52]5[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[CH:54][CH:53]=5)=[N:50][N:51]=4)[CH:43]=[C:44]([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:45]=3)[CH:16]=[CH:17][C:18]=2[C:19]2[C:11]1=[CH:10][CH:9]=[CH:21][CH:20]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 114778562-(9,9-Dioctyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 21982087HCID 21982087, compound

Product 1

HCID 58961748HCID 58961748, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a flask was introduced 2.8 mL of toluene, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (0.80 g, 1.5 mmol), 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole from Example 7 (0.375 g, 0.7 mmole), Aliqua™ 336 (0.15 g, 0.4 mmol) and 1.4 mL of aqueous 2M Na2CO3. This was N2 purged for 1 h. The flask was heated to about 80° C. and tetrakistriphenylphosphine palladium (0) (12 mg, 0.01 mmol) then added under a nitrogen purge. The content of the flask was refluxed for 21 hrs. The reaction flask was allowed to cool to RT and about 5 mL water added and the organic layer separated. The aqueous layer was extracted with 3×15 mL ether. The organic layers were combined and washed successively with saturated NaCl twice and then dried over MgSO4. Concentration gave an oil that was purified by flash chromatography (eluent: 10% ethyl acetate in hexane) and dried as an oil under vacuum for 30 minutes to give 0.59 grams of 2-[3,5-Bis-(9,9-dioctyl-9H-fluoren-2-yl)-phenyl]-5-(4-octyloxy-phenyl)-[1,3,4]oxadiazole.

Workup

  1. customThis was N2 purged for 1 h
  2. custompurge
  3. temperatureThe content of the flask was refluxed for 21 hrs
  4. temperatureto cool to RT
  5. additionabout 5 mL water added
  6. customthe organic layer separated
  7. extractionThe aqueous layer was extracted with 3×15 mL ether
  8. washwashed successively with saturated NaCl twice
  9. dry with materialdried over MgSO4
  10. concentrationConcentration
  11. customgave an oil that
  12. customwas purified by flash chromatography (eluent: 10% ethyl acetate in hexane)
  13. customdried as an oil under vacuum for 30 minutes

Sources & evidence

ORD record
ord-fd7976a5f5f2451cb045890e9cd6afa7
Source dataset
uspto-grants-2007_09
Patent number
US07271406B2

Reaction notes

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