Water → HCID 24796540, compound

HRID 2374692Notes

Reaction equation

HRID 2374692 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[S:9][C:10]([Br:14])=[CH:11][C:12]=1[Br:13].O>C1(C)C=CC=CC=1.C(O)C.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>[Br:13][C:12]1[CH:11]=[C:10]([Br:14])[S:9][C:8]=1[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 76592Thiophene, 2,3,5-tribromo-

Product 1

HCID 24796540HCID 24796540, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (3 mmol) and 100 mL of an aqueous 2N sodium carbonate solution were added to a solution of 2-thiophene-boric acid (5.0 mmol) and 2,3,5-tribromothiophene (100 mmol) in a mixture of 200 mL of toluene and 100 mL of ethanol in a nitrogen atmosphere. The resulting mixture was refluxed for 24 hours. The reaction mixture was combined with water, and extracted with toluene. The extract solution was washed with water, and dried over magnesium sulfate. The solvent was evaporated to obtain a crude product. The crude product was purified by column chromatography and by recrystallization from hexane to obtain the intended product (22.1 mmol) in a 22% yield.

Workup

  1. temperatureThe resulting mixture was refluxed for 24 hours
  2. extractionextracted with toluene
  3. washThe extract solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customto obtain a crude product
  7. customThe crude product was purified by column chromatography and by recrystallization from hexane

Sources & evidence

ORD record
ord-e2ea9a64c734466691ce84198637fcc6
Source dataset
uspto-grants-2008_12
Patent number
US07462726B2

Reaction notes

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