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

HRID 2242290

반응식

HRID 2242290 반응식
[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]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 6389085,5'-Dibromo-2,2'-bithiophene2회HCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)2회

생성물 1

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

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a505cfd53a394aa78ab6c2bc3d5c9449
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671083B2

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