4-Iodobenzoyl chloride → HCID 23512917, compound

HRID 354088Notes

Reaction equation

HRID 354088 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]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:19]=1.[I:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[I:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([C:10]2[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][C:7]=3[S:8][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 743734-Iodobenzoyl chlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23512917HCID 23512917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-methoxy-2-(4-methoxyphenyl)-benzo[b]thiophene 25 (3 g, 11.1 mmol), and ρ-iodobenzoyl chloride in 65 mL of methylene chloride was added aluminum trichloride (2.1 g) in three portions and the reaction was stirred 3 hours. It was then poured into ice-water and extracted with methylene chloride. The combined organic layers was washed with brine and dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography with 3% ethyl acetate-hexanes as eluant the title compound (3.97 g) was obtained.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration, concentration and silica gel column chromatography with 3% ethyl acetate-hexanes as eluant the title compound (3.97 g)
  5. customwas obtained

Sources & evidence

ORD record
ord-f578d8ac7b2b4e35a71d8ccccc8add6f
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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