Sodium Carbonate → Methyl 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-methoxythiophene-2-carboxylate

HRID 450499Notes

Reaction equation

HRID 450499 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:18]1[C:19]([O:35][CH3:36])=[C:20]([C:31]([O:33][CH3:34])=[O:32])[S:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[C:19]([O:35][CH3:36])=[C:20]([C:31]([O:33][CH3:34])=[O:32])[S:21][C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 67502528Methyl 4-bromo-5-(2,4-dichlorophenyl)-3-methoxythio-phene-2-carboxylate

Product 1

HCID 67495513Methyl 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-methoxythiophene-2-carboxylateYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.75 g of (4-chlorophenyl)boronic acid and then, dropwise, 40.93 ml of a 2M solution of Na2CO3 are added to a solution of 16.21 g of the compound of step B) in 110 ml of toluene. Argon is sparged into the reaction mixture for 30 minutes, then 2.36 g of Tetrakis are added and heating is carried out at 110° C. for 18 hours. After cooling to AT, the reaction mixture is rinsed with 80 ml of distilled water, then extraction is carried out with 80 ml of EtOAc, drying is carried out over Na2SO4, and the solvent is evaporated off under vacuum. The reaction crude is purified by silica gel chromatography, elution being carried out with heptane and then with a heptane/EtOAc mixture (85/15; v/v). 13.23 g of the expected compound are obtained.

Workup

  1. customArgon is sparged into the reaction mixture for 30 minutes
  2. addition2.36 g of Tetrakis are added
  3. temperatureheating
  4. temperatureAfter cooling to AT
  5. washthe reaction mixture is rinsed with 80 ml of distilled water
  6. extractionextraction
  7. customdrying
  8. customthe solvent is evaporated off under vacuum
  9. customThe reaction crude
  10. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-16b580ed79724cb39d1800511ed3c0e2
Source dataset
uspto-grants-2013_07
Patent number
US08486971B2

Reaction notes

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