Reaction #715759

Reaction equation

K3PO4

4-Bromo-N-methyl-2-nitroaniline

2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

biphenyl-2-yldicyclohexylphosphine

→

crude product

Yield 169.4%

N4-Methyl-3,3′-dinitrobiphenyl-4,4′-diamine

Yield 169.4%

Solvents

DME H2O

Conditions

Workup

1. 1
   Otherthe mixture was purged with nitrogen
2. 2
   Otherthen degassed by sonication
3. 3
   workup.ADDITIONPd(OAc)2 (5 mg, 5 mol %) was added
4. 4
   workup.ADDITIONThe cooled mixture was diluted with EtOAc and H2O
5. 5
   OtherThe organics were separated
6. 6
   Extractionthe aqueous layer extracted with EtOAc (3×50 mL)
7. 7
   WashThe combined organic extracts were washed with brine
8. 8
   Dryingdried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated in vacuo

Procedure

4-Bromo-N-methyl-2-nitroaniline (100 mg, 0.43 mmol), 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (115 mg, 0.43 mmol), biphenyl-2-yldicyclohexylphosphine (30 mg, 20 mol %) and K3PO4 (275 mg, 1.3 mmol) were suspended in DME-H2O (4:1, 5 mL), the mixture was purged with nitrogen then degassed by sonication. Pd(OAc)2 (5 mg, 5 mol %) was added, and the mixture heated to 130° C. for 10 min under microwave irradiation. The cooled mixture was diluted with EtOAc and H2O. The organics were separated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the crude product as a dark brown solid (210 mg). The crude material was taken on without further purification.

Source