Reaction #1509643

Reaction equation

(4-(diphenylamino)phenyl)boronic acid

4-iodo-1-bromobenzene

Na2CO3

→

Compound 35

Yield 87.0%

4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine

Yield 87.0%

Solvents

THF H2O

Conditions

Workup

1. 1
   Otherwas degassed
2. 2
   Temperaturethe resulting mixture was heated
3. 3
   Temperatureat reflux overnight under an argon atmosphere
4. 4
   TemperatureAfter cooling
5. 5
   workup.ADDITIONthe mixture was poured into dichloromethane (150 mL)
6. 6
   Washwashed with water (2×150 mL) and brine (100 mL)
7. 7
   DryingThe organic phase was dried over Na2SO4
8. 8
   Otherpurified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1)
9. 9
   Otherthen recrystallized in dichloromethane/methanol

Procedure

A mixture of (4-(diphenylamino)phenyl)boronic acid (1.5 g, 5.19 mmol), 4-iodo-1-bromobenzene (1.33 g, 4.71 mmol), Na2CO3 (1.78 g, 16.8 mmol) and Pd(PPh3)4 (0.163 g, 0.141 mmol) in THF/H2O (28 mL/17 mL) was degassed and the resulting mixture was heated at reflux overnight under an argon atmosphere. After cooling, the mixture was poured into dichloromethane (150 mL), then washed with water (2×150 mL) and brine (100 mL). The organic phase was dried over Na2SO4, purified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1) then recrystallized in dichloromethane/methanol to afford a white solid (Compound 35)(1.64 g, in 87% yield).

Source