Chloride → 5-Chloro-2-(4-methoxyphenyl)-3-[4-(3-diethylaminopropyloxy)benzoyl]benzofuran

HRID 346878Notes

Reaction equation

HRID 346878 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:18]=1.[CH2:19]([N:21]([CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:22][CH3:23])[CH3:20].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)=[C:7]([C:32](=[O:33])[C:31]3[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[CH:36][CH:35]=3)[C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 102362405-Chloro-2-(4-methoxyphenyl)benzofuranHCID 214352614-(3-Diethylaminopropoxy)benzoyl chloride

Product 1

HCID 99353805-Chloro-2-(4-methoxyphenyl)-3-[4-(3-diethylaminopropyloxy)benzoyl]benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-2-(4-methoxyphenyl)benzofuran (1 g, 3.9 mmol) in DCM (100 mL) was stirred at 0° C. under nitrogen. The compound of Example 2(iii) (1.68 g, 6.9 mmol) was added followed by the drop-wise addition of tinIV chloride solution (1M DCM, 11.6 mmol). The colour became a deep red and the reaction was stirred at RT. for 3 hrs. The resulting suspension was poured onto ice-water (250 mL) and the organic portion separated. The aqueous layer was extracted with DCM and the organic portions were combined, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography to give the title compound as a yellow tar (1.34 g, 72%).

Workup

  1. additionThe resulting suspension was poured onto ice-water (250 mL)
  2. customthe organic portion separated
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-cd186bb2b08142a1a2cd06e7253f23f9
Source dataset
uspto-grants-2007_02
Patent number
US07173061B2

Reaction notes

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