p-Anisoyl chloride → Methanone, (5-bromo-2-thienyl)(4-methoxyphenyl)-

HRID 1153786Notes

Reaction equation

HRID 1153786 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1>C(Cl)Cl>[Br:1][C:2]1[S:3][C:4]([C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 138512-Bromothiophene

Product 1

HCID 298606Methanone, (5-bromo-2-thienyl)(4-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0°-5° C.) solution of 2-bromothiophene (32.6 g, 0.2 mol) and p-methoxybenzoyl chloride (34.1 g, 0.2 mol) in methylene chloride was added anhydrous stannic chloride (52 g, 0.2 mol) dropwise over about one hour. When addition was complete, the cooling bath was removed and the solution was stirred for an additional two hours. A solution of water (90 mL) and concentrated hydrochloric acid (10 mL) was added dropwise and the layers were separated. The organic layer was washed with water, saturated sodium chloride solution and dried (MgSO4). Removal of the solvent in vacuo and collection of the slide with the aid of hexane gave 48.5 g, of gray powder, m.p. 97°-99° C. A sample was recrystallized from ligroin for analysis.

Workup

  1. additionWhen addition
  2. customthe cooling bath was removed
  3. additionA solution of water (90 mL) and concentrated hydrochloric acid (10 mL) was added dropwise
  4. customthe layers were separated
  5. washThe organic layer was washed with water, saturated sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvent
  8. customin vacuo and collection of the slide with the aid of hexane
  9. customgave 48.5 g
  10. customA sample was recrystallized from ligroin for analysis

Sources & evidence

ORD record
ord-e7157db65c4645a895023c98da45370a
Source dataset
uspto-grants-1984_12
Patent number
US04486444

Reaction notes

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