Sodium Carbonate → HCID 86646876, compound

HRID 1926175Notes

Reaction equation

HRID 1926175 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:22]=[CH:21][C:20]3[C:11](=[C:12]([C:44]#[C:45][Si:46]([CH:53]([CH3:55])[CH3:54])([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])[C:13]4[C:18]([C:19]=3[C:23]#[C:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=4)[CH:10]=2)O1.Br[C:58]1[S:62][CH:61]=[C:60]([CH:63]=[O:64])[CH:59]=1.[C:65](=[O:68])([O-])[O-].[Na+].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:63]([C:60]1[CH:59]=[C:58]([C:16]2[CH:15]=[CH:14][C:13]3[C:18](=[C:19]([C:23]#[C:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[C:20]4[C:11]([C:12]=3[C:44]#[C:45][Si:46]([CH:50]([CH3:52])[CH3:51])([CH:47]([CH3:49])[CH3:48])[CH:53]([CH3:54])[CH3:55])=[CH:10][C:9]([C:61]3[S:62][CH:58]=[C:59]([CH:65]=[O:68])[CH:60]=3)=[CH:22][CH:21]=4)[CH:17]=2)[S:62][CH:61]=1)=[O:64]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 122848945-Bromothiophene-3-carbaldehydeHCID 57567773HCID 57567773, compound

Product 1

HCID 86646876HCID 86646876, compound

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A 250 mL Schlenk flask is charged with 2,6-bis-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (2.00 mmol), 5-bromothiophene-3-carbaldehyde (UkrOrgSynthesis Ltd., Kiev, Ukraine) (5.00 mmol), sodium carbonate (10 mmol), ALIQUAT 336 (0.09 g, a mixture of [CH3(CH2)9]3NCH3+Cl− and [CH3(CH2)7]3NCH3+Cl−, used as a phase transfer catalyst), distilled water (25 mL), and toluene (100 mL). The mixture is degassed under a Schlenk line to remove oxygen. Tetrakis(triphenylphosphine)palladium(0) (0.02 mmol) is then added under nitrogen flow. The mixture is stirred under nitrogen at 90° C. for 20 hours. The upper toluene solution is isolated and washed with DI water (100 mL×3). After being concentrated to about 25 mL, it is quenched in methanol (MeOH) (100 mL). The precipitate is collected by filtration and is purified by zone sublimation or column chromatography (silica gel, chloroform or hexane).

Workup

  1. additiona mixture of [CH3(CH2)9]3NCH3+Cl− and [CH3(CH2)7]3NCH3+Cl−
  2. distillationdistilled water (25 mL), and toluene (100 mL)
  3. customThe mixture is degassed under a Schlenk line
  4. customto remove oxygen
  5. washwashed with DI water (100 mL×3)
  6. concentrationAfter being concentrated to about 25 mL, it
  7. customis quenched in methanol (MeOH) (100 mL)
  8. filtrationThe precipitate is collected by filtration
  9. customis purified by zone sublimation or column chromatography (silica gel, chloroform or hexane)

Sources & evidence

ORD record
ord-28cb3f545f4247bba68bbe103f40fd94
Source dataset
uspto-grants-2012_05
Patent number
US08178873B2

Reaction notes

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