Reaktion #801846

Reaktionsgleichung

dimethyl 5-bromoisophthalate

2-chlorophenylboronic acid

2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

potassium phosphate

→

Dimethyl 2′-chlorobiphenyl-3,5-dicarboxylate

Lösungsmittel

toluene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to RT
2. 2
   FiltrationThe solid was filtered off with suction
3. 3
   Waschenthe residue was washed three times with in each case 10 ml of ethyl acetate
4. 4
   WaschenThe combined filtrates were washed twice with in each case 10 ml of water
5. 5
   TrocknenThe organic phase was dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified chromatographically [Method 19]

Vorschrift

Under argon, 500 mg (1.83 mmol) of dimethyl 5-bromoisophthalate together with 429 mg (2.75 mmol) of 2-chlorophenylboronic acid were dissolved in 8 ml of toluene, and 72 mg (0.18 mmol) of 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl, 84 mg (0.09 mmol) of tris(dibenzylideneacetone)dipalladium and 777 mg (3.66 mmol) of potassium phosphate were added successively. The mixture was heated to 110° C. and stirred at this temperature for 20 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate. The solid was filtered off with suction and the residue was washed three times with in each case 10 ml of ethyl acetate. The combined filtrates were washed twice with in each case 10 ml of water. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically [Method 19]. This gave 305 mg (55% of theory) of the target compound.

Quelle