Potassium Carbonate → 2,5-Bis-{5'[6-(tert-butyldimethylsilanyloxy)-hexyl]-[2,2']bithiophenyl-5-yl}-thieno[3,2-b]thiophene

HRID 644112Notes

Reaction equation

HRID 644112 reaction equation
Br[C:2]1[S:6][C:5]2[CH:7]=[C:8](Br)[S:9][C:4]=2[CH:3]=1.[C:11]([Si:15]([CH3:43])([CH3:42])[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[S:27][C:26]([C:28]2[S:29][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:32]=2)=[CH:25][CH:24]=1)([CH3:14])([CH3:13])[CH3:12].[C:44](=[O:47])([O-])[O-].[K+].[K+]>C1COCC1.O.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>[Si:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[S:27][C:26]([C:28]2[S:29][C:30]([C:2]3[S:6][C:5]4[CH:7]=[C:8]([C:30]5[S:29][C:28]([C:26]6[S:27][C:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:44][O:47][Si:15]([C:11]([CH3:12])([CH3:14])[CH3:13])([CH3:43])[CH3:42])=[CH:24][CH:25]=6)=[CH:32][CH:31]=5)[S:9][C:4]=4[CH:3]=3)=[CH:31][CH:32]=2)=[CH:25][CH:24]=1)([C:11]([CH3:14])([CH3:12])[CH3:13])([CH3:43])[CH3:42]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 35974552,5-Dibromothieno(3,2-b)thiopheneHCID 588073092-{5'-[6-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-[2,2']bithiophenyl-5-yl}-4,4,5,5-tetramethyl-[1,3,2}dioxaborolane

Product 1

HCID 589916242,5-Bis-{5'[6-(tert-butyldimethylsilanyloxy)-hexyl]-[2,2']bithiophenyl-5-yl}-thieno[3,2-b]thiophene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.05 g) was added to a solution 2,5-dibromothieno[3,2-b]thiophene (0.10 g, 0.34 mmol) in dry THF (30 ml), with stirring, under nitrogen. After 20 min, 2-{5′-[6-(tert-butyl-dimethyl-silanyloxy)-hexyl]-[2,2′]bithiophenyl-5-yl}-4,4,5,5-tetramethyl-[1,3,2}dioxaborolane (0.51 g, 1.01 mmol) and a solution of potassium carbonate (0.28 g, 2.03 mmol) in water (10 ml) were added. The resultant mixture was heated at reflux for 1.5 h. After cooling, water (100 ml) was added and the precipitate filtered off, washed with water and diethyl ether, to give a yellow solid, which was recrystallised with toluene to offer yellow crystals (0.17 g, 57%).

Workup

  1. temperatureat reflux for 1.5 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate filtered off
  4. washwashed with water and diethyl ether
  5. customto give a yellow solid, which
  6. customwas recrystallised with toluene

Sources & evidence

ORD record
ord-81151031f8a249ada13286f3cb2c58b2
Source dataset
uspto-grants-2010_04
Patent number
US07700643B2

Reaction notes

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