Reaction #44368

Reaction equation

4-bromo-2-chlorobenzoic acid

5-chloro-2-methoxybenzoic acid

sodium carbonate

dioxan

→

sub-title compound

Yield 79.2%

3,5′-dichloro-2′-methoxy-[1,1′-biphenyl]-4-carboxylic acid

Yield 79.2%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 16 h
3. 3
   Filtrationfiltered (hyflo)
4. 4
   ConcentrationThe filtrate was concentrated in vacuo
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   workup.ADDITIONThe suspension was made basic by addition of dilute NaOH
7. 7
   OtherThe aqueous layer was separated
8. 8
   Extractionextracted with EtOAc
9. 9
   Dryingdried (MgSO4)
10. 10
    Otherevaporated in vacuo

Procedure

4-bromo-2-chlorobenzoic acid (0.4 g), 5-chloro-2-methoxybenzoic acid (0.4 g), Pd(dppf)Cl2 (0.12 g), sodium carbonate (0.9 g), dioxan (15 ml) and methanol (5 ml) were charged to a flask and heated at reflux for 16 h. Cooled to room temp and filtered (hyflo). The filtrate was concentrated in vacuo, then dissolved in ethyl acetate. The suspension was made basic by addition of dilute NaOH. The aqueous layer was separated and acidified using 2M HCl, extracted with EtOAc, dried (MgSO4) and evaporated in vacuo to give the sub-title compound Yield 0.4 g

Source