p-Anisoyl chloride → HCID 21915324, compound

HRID 568517Notes

Reaction equation

HRID 568517 reaction equation
C1([Li])C=CC=CC=1.[Br:8][C:9]1[CH:13]=[CH:12][S:11][CH:10]=1.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>CCOCC.O1CCCC1>[Br:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:20]([C:19]1[CH:23]=[CH:24][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)=[O:21]

Participants

6

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 133833-BromothiopheneHCID 178506676HCID 178506676, compound

Product 1

HCID 21915324HCID 21915324, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenyllithium (67 ml, 1.65M in ether/benzene) was added dropwise to a solution of 16.3 g of 3-bromothiophene in 100 ml of dry ether at room temperature under nitrogen. After the addition, the solution was stirred overnight under nitrogen. The resultant solution was then added dropwise to a solution of p-methoxybenzoyl chloride (20.5 g) in 80 ml of tetrahydrofuran at -70° C. over two hours and stirring was further continued for two hours at the same temperature. The reaction was then quenched with water, the organics were extracted into ether, and the ether phase was washed with 10% aqueous sodium hydroxide solution and water and dried over anhydrous magnesium sulfate. Upon evaporation of the solvent, oily liquid was obtained which was chromatographed by high performance liquid chromatography with 5% ethyl acetate/hexane used as an eluent. Appropriate fractions were combined and evaporated to give crystals which were recrystallized from ether/hexane (yield 11.9 g).

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. waitwas further continued for two hours at the same temperature
  4. customThe reaction was then quenched with water
  5. extractionthe organics were extracted into ether
  6. washthe ether phase was washed with 10% aqueous sodium hydroxide solution and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customUpon evaporation of the solvent
  9. customoily liquid was obtained which
  10. customwas chromatographed by high performance liquid chromatography with 5% ethyl acetate/hexane
  11. customevaporated
  12. customto give crystals which
  13. customwere recrystallized from ether/hexane (yield 11.9 g)

Sources & evidence

ORD record
ord-e6def3c999e64ecfb0d5beb532452370
Source dataset
uspto-grants-1988_03
Patent number
US04728651

Reaction notes

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