Benzoyl chloride → [6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophen-3-yl](phenyl)methanone

HRID 1956804Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ClCl.[Al+3].[Cl-].[Cl-].[Cl-]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:27])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3 g (11.1 mmol) of 2-(4-methoxyphenyl)-6-methoxybenzo[b]thiophene and 1.55 g (11.1 mmol) of benzoyl chloride were suspended in 150 mL of CH2 Cl2 and cooled to 0° C. The reaction mixture was vigorously stirred and 1.6 g (12 mmol) of AlCl3 was added in several portions over a ten minute time period. The reaction was allowed to proceed for one hour, after which 1 L of water was added to quench the reaction. The organic layer was separated and washed with 100 mL of 1N NaOH, 100 mL of brine, dried by filtration through anhydrous K2CO3, and evaporated to dryness. The crude product was crystallized twice from MeOH. This yielded 1.85 g of the title compound as white crystalline solid.

Workup

customto quench
customthe reaction
customThe organic layer was separated
washwashed with 100 mL of 1N NaOH, 100 mL of brine
dry with materialdried by filtration through anhydrous K2CO3
customevaporated to dryness
customThe crude product was crystallized twice from MeOH

Sources & evidence

ORD record: ord-3feffe29b95842d39d9afa942625a47c
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780648

Reaction notes

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