Hexane → 3-(4-Chlorobenzoyl)-2-(4-chlorophenylthio)-5-dimethoxymethylthiophene

HRID 1058651Notes

Reaction equation

HRID 1058651 reaction equation
Br[C:2]1[CH:6]=[C:5]([CH:7]([O:10][CH3:11])[O:8][CH3:9])[S:4][C:3]=1[S:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.C([Li])CCC.CCCCCC.[Cl:31][C:32]1[CH:43]=[CH:42][C:35]([C:36](N(OC)C)=[O:37])=[CH:34][CH:33]=1>O1CCCC1.O>[Cl:31][C:32]1[CH:43]=[CH:42][C:35]([C:36]([C:2]2[CH:6]=[C:5]([CH:7]([O:10][CH3:11])[O:8][CH3:9])[S:4][C:3]=2[S:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[O:37])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 112756634-Chloro-N-methoxy-N-methylbenzamideHCID 186689273-Bromo-2-(4-chlorophenylthio)-5-dimethoxymethylthiopheneHCID 178418339Butyllithium

Product 1

HCID 186690093-(4-Chlorobenzoyl)-2-(4-chlorophenylthio)-5-dimethoxymethylthiopheneYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In an argon atmosphere, 3-bromo-2-(4-chlorophenylthio)-5-dimethoxymethylthiophene (500 mg, 1.32 mmol) obtained in Example 90 was dissolved in tetrahydrofuran (6 mL) and cooled to −78° C. n-Butyl lithium (a 1.6 mol/L hexane solution, 0.81 mL, 1.3 mmol) and tetrahydrofuran (1 mL) solution of 4-chloro-N-methoxy-N-methylbenzamide (528 mg, 2.64 mmol) were added thereto, followed by stirring for 10 minutes. Water was added to the reaction liquid and the product was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (15:1 hexane/ethyl acetate) to give 3-(4-chlorobenzoyl)-2-(4-chlorophenylthio)-5-dimethoxymethylthiophene (345 mg, 60%).

Workup

  1. additionwere added
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (15:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8bf48d9fca4f4237899c4e137fe698a0
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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