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

HRID 2242290

Reaction equation

HRID 2242290 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a505cfd53a394aa78ab6c2bc3d5c9449
Source dataset
uspto-grants-2010_03
Patent number
US07671083B2

Linked notes

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