1,2-Dimethoxyethane → 5,5'-Bis[4-(octyloxy)phenyl]-2,2'-bithiophene

HRID 2242290

反応式

HRID 2242290 の反応式
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:20]1[S:24][C:23]([C:25]2[S:26][C:27](Br)=[CH:28][CH:29]=2)=[CH:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CO[CH2:41][CH2:42][O:43][CH3:44]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2[S:24][C:23]([C:25]3[S:26][C:27]([C:10]4[CH:11]=[CH:12][C:42]([O:43][CH2:44][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:41][CH:15]=4)=[CH:28][CH:29]=3)=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 6389085,5'-Dibromo-2,2'-bithiophene2 回HCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)2 回

生成物 1

HCID 590273195,5'-Bis[4-(octyloxy)phenyl]-2,2'-bithiophene

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 4-octyloxy-phenylboronic acid (Compound 7) (12.0 g, 0.048 mol), 5,5′-dibromo-2,2′-bithiophene (Compound 8) (7.23 g, 0.022 mol), bis(triphenylphosphine) palladium (II) dichloride (0.39 g, 0.56 mmol), and potassium phosphate (15.3 g, 0.072 mol), 160 mL ethylene glycol dimethylether and 50 mL water were added. After heating for 4 hours at 70° C., the reaction mixture was cooled on an ice bath. The solids were filtered and washed with a small amount of chloroform. The solids were suspended in 600 mL water, stirred for 30 minutes, and then filtered. This washing procedure was repeated with methanol. Following two crystallizations from trifluorotoluene using decolorizing charcoal, 5,5′-di(4-octyloxy-phenyl)-2,2′-bithiophene (Compound 4) was isolated as yellow/orange crystals (10.34 g, 81%).

後処理

  1. additionwere added
  2. temperaturethe reaction mixture was cooled on an ice bath
  3. filtrationThe solids were filtered
  4. washwashed with a small amount of chloroform
  5. filtrationfiltered
  6. customtwo crystallizations from trifluorotoluene using

出典と根拠

ORDレコード
ord-a505cfd53a394aa78ab6c2bc3d5c9449
出典データセット
uspto-grants-2010_03
特許番号
US07671083B2

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