Reaction #1509639

Reaction equation

tri-tert-butyl phosphine

Di-p-tolylamine

4,4′-dibromobiphenyl

Sodium tert-butoxide

→

material

Yield 3.0%

4′-bromo-N,N-di-p-tolylbiphenyl-4-amine

Yield 3.0%

Solvents

—

hexanes

—

hexanes

ethyl acetate

Conditions

Workup

1. 1
   Otherwas degassed in toluene (anhydrous, 50 mL) for 20 minutes
2. 2
   Otherthe mixture was further degassed for 15 minutes
3. 3
   Othermixture was further degassed for 10 minutes
4. 4
   TemperatureAfter cooling
5. 5
   workup.ADDITIONthe mixture was poured into DCM, and solids
6. 6
   Filtrationwere filtered off
7. 7
   WashFiltrate was washed with water and brine
8. 8
   OtherThe organic layer was collected
9. 9
   Dryingdried over sodium sulfate

Procedure

A mixture of tris(dibenzylideneacetone)dipalladium (353 mg, 0.385 mmol), and tri-tert-butyl phosphine (3.11 g of a 10% solution in hexanes) was degassed in toluene (anhydrous, 50 mL) for 20 minutes. Di-p-tolylamine (3.00 g, 15.2 mmol), and 4,4′-dibromobiphenyl (4.80 g, 15.4 mmol) were added and the mixture was further degassed for 15 minutes. Sodium tert-butoxide (2.4 g, 25 mmol) was added, and mixture was further degassed for 10 minutes. The whole was heated overnight at 120° C. under argon. After cooling, the mixture was poured into DCM, and solids were filtered off. Filtrate was washed with water and brine. The organic layer was collected and dried over sodium sulfate, then loaded onto silica gel. A flash column (gradient of 2-20% ethyl acetate in hexanes) gave 190 mg of material (3% yield); confirmed pure by HNMR.

Source