Reaktion #547271

Reaktionsgleichung

4-difluoromethoxy-1-iodo-benzene

dichloromethane

dichloromethane

5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester

5-methyl-4-[4-(4,4,5,5-tetramethyl-[1, 3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester

4-difluoromethoxy-1-iodo-benzene

cesium carbonate

→

compound 128

Ausbeute 57.2%

4-(4′-difluoromethoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Ausbeute 57.2%

Lösungsmittel

1,4-dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenthe mixture was concentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
4. 4
   Waschenwashed with water and brine
5. 5
   Sonstigedried
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Sonstigethe residue was purified by flash chromatography
8. 8
   Sonstigepetrol (40–60°)/diethyl ether 9

Vorschrift

A degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (119) (200 mg, 0.54 mmoles), 4-difluoromethoxy-1-iodo-benzene (175 mg, 0.65 mmoles), 2M aqueous cesium carbonate (0.81 ml) and), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (20 mg) in 1,4-dioxan (10 ml), under an argon atmosphere was heated at 80° C. for 20 h. Further quantities of 4-difluoromethoxy-1-iodo-benzene (87.5 mg, 0.0.27 mmoles) and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (10 mg) were added and heating at 80° C. was continued for 4 hours. After cooling, the mixture was concentrated. The residue was dissolved in dichloromethane and washed with water and brine, and dried. The solvent was evaporated and the residue was purified by flash chromatography using petrol (40–60°)/diethyl ether 9:1v/v as eluent to afford compound 128(120 mg) as a wax. LC/MS System A; Rt=4.14 mins.

Quelle