Sodium Carbonate → 2,5-Bis(3',4'-dimethoxyphenyl)thiophene

HRID 538729Notes

Reaction equation

HRID 538729 reaction equation
Br[C:2]1[S:3][C:4](Br)=[CH:5][CH:6]=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].[C:21]([O-:24])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:2]2[S:3][C:4]([C:13]3[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[C:15]([O:24][CH3:21])[CH:14]=3)=[CH:5][CH:6]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 184532,5-DibromothiopheneHCID 27347023,4-Dimethoxyphenylboronic acid

Product 1

HCID 682939712,5-Bis(3',4'-dimethoxyphenyl)thiophene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,5-dibromothiophene (14) (242 mg, 1 mmol), (3,4-dimethoxy phenyl)boronic acid (15) (455 mg, 2.5 mmol), and Pd(PPh3)4 (58 mg, 0.05 mmol) in dioxane (10 mL) was added Na2CO3 (12 mL, 2.0 M aqueous solution). The resultant mixture was purged with nitrogen and stirred rapidly while heating at 90° C. overnight. The reaction mixture was cooled to 23° C., acidified with 1M HCl and extracted with EtOAc. The combined organic extracts were washed with H2O, dried over MgSO4, filtered and concentrated under reduced pressure. 2,5-bis(3′,4′-dimethoxyphenyl)thiophene (16) was obtained quantitatively as a green-yellow solid after the purification by column chromatography (10%-20% EtOAc in hexanes).

Workup

  1. customThe resultant mixture was purged with nitrogen
  2. temperatureThe reaction mixture was cooled to 23° C.
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34c94147d5294130a2e1edbadc140268
Source dataset
uspto-grants-2014_10
Patent number
US08865754B2

Reaction notes

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