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

HRID 644112ノート

反応式

HRID 644112 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-81151031f8a249ada13286f3cb2c58b2
出典データセット
uspto-grants-2010_04
特許番号
US07700643B2

反応ノート

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