Potassium Carbonate → (2,4-Dichloro-phenyl)(6-iodo-benzofuran-2-yl)-methanone

HRID 1717665Notes

Reaction equation

HRID 1717665 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([OH:10])[CH:3]=1.Cl[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:13]([C:12]1[O:10][C:4]2[CH:3]=[C:2]([I:1])[CH:9]=[CH:8][C:5]=2[CH:6]=1)=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 202502,2',4'-TrichloroacetophenoneHCID 183515132-Hydroxy-4-iodobenzaldehyde

Product 1

HCID 59788945(2,4-Dichloro-phenyl)(6-iodo-benzofuran-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-2-hydroxy-benzaldehyde (5.4 g, 22 mmol) and 2-chloro-1-(2,4-dichlorophenyl)ethanone (11.2 g, 50.0 mmol) in anhydrous N,N-dimethylformamide (100 mL) was added K2CO3 (12.0 g, 86.9 mmol). The dark brown reaction mixture was stirred at 90 C for 48 h, then poured onto water (150 mL) and extracted with ethyl acetate. The solvent was removed under reduced pressure and the residue was purified by column chromatography, eluting with 50% hexanes in dichloromethane. The desired product was obtained as an orange solid (2.06 g, 23%). 1H-NMR (CDCl3) δ 7.98 (s, 1H), 7.70 (dd, J=8.3, 1.3 Hz, 1H), 7.54-7.21 (m, 5H).

Workup

  1. additionpoured onto water (150 mL)
  2. extractionextracted with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography
  5. washeluting with 50% hexanes in dichloromethane

Sources & evidence

ORD record
ord-54bc2aea2ae146459446a38fe9645115
Source dataset
uspto-grants-2010_09
Patent number
US07803956B2

Reaction notes

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