Water → HCID 68285842, compound

HRID 1518700Notes

Reaction equation

HRID 1518700 reaction equation
[Br:1][C:2]1[CH:6]=[C:5](Br)[S:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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:1][C:2]1[CH:6]=[C:5]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)[S:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 13177180Ethyl 3,5-dibromothiophene-2-carboxylate

Product 1

HCID 68285842HCID 68285842, compoundYield 68.18%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 3,5-dibromothiophene-2-carboxylate (Prepared according to procedure reported in J. Chem. Soc. Perkin Trans-1: Organic and Bioorganic Chemistry (1972-1999), 1973, p 1766-1770), 2.0 g (6.36 mmol) in a mixture of toluene:water (35:2 ml) was added (4-chlorophenyl)boronic acid [0.99 g, 6.36 mmol] and potassium carbonate (1.76 g, 12.73 mmol) at 25° C. Nitrogen gas was bubbled through reaction mixture for 15 minutes. To the reaction mixture was then added tetrakis(triphenylphosphine)palladium(0) (0.37 g, 0.31 mmol) under nitrogen atmosphere and the reaction mixture was heated at about 95 to about 100° C. for 3 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite and the celite cake was washed with ethyl acetate (50 ml). The filtrate so obtained was concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using and 6% ethyl acetate in hexanes as an eluent to obtain the title compound (1.5 g, 68.18%).

Workup

  1. customNitrogen gas was bubbled through reaction mixture for 15 minutes
  2. filtrationfiltered through celite
  3. washthe celite cake was washed with ethyl acetate (50 ml)
  4. customThe filtrate so obtained
  5. concentrationwas concentrated under reduced pressure
  6. customto obtain a crude product, which
  7. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-973726d53c484aab95151f0a499f89b5
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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