4-Cyanobenzoyl chloride → 4-[[6-Methoxy-2-(4-methylphenyl)-3-benzofuranyl]carbonyl]benzonitrile

HRID 234789Notes

Reaction equation

HRID 234789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[O:8][C:7]=2[CH:18]=1.[C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)#[N:20]>Cl[Ti](Cl)(Cl)Cl.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:25]([C:24]3[CH:28]=[CH:29][C:21]([C:19]#[N:20])=[CH:22][CH:23]=3)=[O:26])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[O:8][C:7]=2[CH:18]=1

Participants

5

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 189255446-Methoxy-2-(4-methylphenyl)-1-benzofuran

Product 1

HCID 189255394-[[6-Methoxy-2-(4-methylphenyl)-3-benzofuranyl]carbonyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

One gram (4.2 mmol) of 6-Methoxy-2-(4methylphenyl)benzo[b]furan was dissolved 25 mL of dichloromethane and 830 mg (5.0 mmol) of 4-cyanobenzoyl chloride was added. The reaction was stirred and kept under a nitrogen atmosphere. 2.75 mL (25 mmol) of TiCl4 was slowly added to the reaction mixture. The reaction was allowed to proceed for four hours and quenched by the addition of 5 mL of methanol (MeOH). The solvents were removed by evaporation and the crude material was chromatographed on a silica gel column eluted with hexane-EtOAc (9:1). The desired fractions were determined by tlc and combined and evaporated to a solid. The resulting product was crystallized from diethyl ether (Et2O). This yielded 325 mg of the title compound as yellow powder.

Workup

  1. additionwas added
  2. customquenched by the addition of 5 mL of methanol (MeOH)
  3. customThe solvents were removed by evaporation
  4. customthe crude material was chromatographed on a silica gel column
  5. washeluted with hexane-EtOAc (9:1)
  6. customevaporated to a solid
  7. customThe resulting product was crystallized from diethyl ether (Et2O)

Sources & evidence

ORD record
ord-6aebd1ce5d9246708b3075d226fa4c31
Source dataset
uspto-grants-1997_01
Patent number
US05596106

Reaction notes

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