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

HRID 644112노트

반응식

HRID 644112 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-81151031f8a249ada13286f3cb2c58b2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700643B2

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