2,2′-Dibromobiphenyl

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an atmosphere of argon, 2,2′-dibromobiphenyl (9.5 g, 30 mmole), phenylboronic acid (3.7 g, 30 mmole) and tetrakis(triphenyl-phosphine)palladium(0) (1.0 g, 0.87 mmole, 3% Pd) were dissolved into toluene (75 ml). To the obtained solution, an aqueous solution of sodium carbonate (9.7 g, 92 mmole, 3 eq/46 ml) was added. The resultant solution was heated under refluxing for 10 hours and left standing for one night. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a dark yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane, successively) and a colorless oil (6.5 g, 70%) was obtained. under refluxing for 10 hours left standing for one night The formed organic layer was separated washed with a saturated aqueous solution of sodium chloride (50 ml) dried over anhydrous magnesium sulfate Then, the solvent was removed by distillation a dark yellow oil was obtained The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure for Compound 3, (9-phenyl-9H-carbazol-3-yl)boronic acid (1.84 g, 6.41 mmol), 2,2′-dibromo-1,1′-biphenyl (4.00 g, 12.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.296 g, 0.257 mmol), Na2CO3 (2.54 g, 24.0 mmol), H2O (24 mL) and THF (40 mL) yielded Compound 9 (1.69 g, 56%) as a colorless solid after flash chromatography (SiO2, 19:1-hexanes: CH2Cl2): confirmed by LCMS (APCI): calculated for C30H20NBr (M+): 474; Found: 474.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure for Compound 3, (9-phenyl-9H-carbazol-3-yl)boronic acid (1.84 g, 6.41 mmol), 2,2′-dibromo-1,1′-biphenyl (4.00 g, 12.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.296 g, 0.257 mmol), Na2CO3 (2.54 g, 24.0 mmol), H2O (24 mL) and THF (40 mL) yielded Compound 9 (1.69 g, 56%) as a colorless solid after flash chromatography (SiO2, 19:1-hexanes: CH2Cl2): confirmed by LCMS (APCI): calculated for C30H20NBr (M+): 474; Found: 474.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of Compound 2 (3.00 g, 7.57 mmol), 2,2′-dibromo-1,1′-biphenyl (4.72 g, 15.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.350 g, 0.303 mmol), Na2CO3 (3.18 g, 30.0 mmol), H2O (30 mL) and tetrahydrofuran (THF) (50 mL) was degassed with argon for about 44 min while stirring. The reaction mixture was then maintained under argon at about 80° C. while stirring. Upon confirming consumption of the starting material by TLC (SiO2, 19:1-CH2Cl2:acetone), the reaction was cooled to RT and poured over CH2Cl2 (ca. 250 mL). The organics were then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified via flash chromatography (SiO2, 100% CH2Cl2 to 39:1-CH2Cl2:acetone) to yield Compound 3 (2.34 g, 62%) as an off-white foam: confirmed by LCMS (APCI): calculated for C31H21BrN2 (M+): 501; Found: 501. was degassed with argon for about 44 min while stirring consumption of the starting material by TLC (SiO2, 19:1-CH2Cl2:acetone) the reaction was cooled to RT poured over CH2Cl2 (ca. 250 mL) The organics were then washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude product was purified via flash chromatography (SiO2, 100% CH2Cl2 to 39:1-CH2Cl2:acetone)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 ml of a 1.6M solution of butyllithium in hexane are added dropwise to a solution of 11.4 g (36.54 mmol) of 2,2'-dibromobiphenyl in 60 ml of diethyl ether. The mixture is then stirred for 24 hours at 20° C. To this is then added, at 0C, a solution of 8.6 g (36.5 mmol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorine in 30 ml of o-xylene. The mixture is then stirred for a further 2 hours at 25° C. and 3 hours at 50° C. The mixture is cooled to room temperature and 100 ml of water are carefully added. The mixture is neutralized with dilute hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and concentrated under reduced pressure. By crystallization of the residue with 2-butanone, 11.8 g (90%) of colorless crystals having melting point 152° to 155° C. are obtained. The mixture is then stirred for a further 2 hours at 25° C. and 3 hours at 50° C The mixture is cooled to room temperature the organic phase is separated off dried with sodium sulfate concentrated under reduced pressure By crystallization of the residue with 2-butanone, 11.8 g (90%) of colorless crystals are obtained

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 ml of a 1.6M solution of butyllithium in hexane are added dropwise to a solution of 11.4 g (36.54 mmol) of 2,2'-dibromobiphenyl in 60 ml of diethyl ether. The mixture is then stirred for 24 hours at 20° C. To this is then added, at 0C, a solution of 8.6 g (36.5 mmol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorine in 30 ml of o-xylene. The mixture is then stirred for a further 2 hours at 25° C. and 3 hours at 50° C. The mixture is cooled to room temperature and 100 ml of water are carefully added. The mixture is neutralized with dilute hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and concentrated under reduced pressure. By crystallization of the residue with 2-butanone, 11.8 g (90%) of colorless crystals having melting point 152° to 155° C. are obtained. The mixture is then stirred for a further 2 hours at 25° C. and 3 hours at 50° C The mixture is cooled to room temperature the organic phase is separated off dried with sodium sulfate concentrated under reduced pressure By crystallization of the residue with 2-butanone, 11.8 g (90%) of colorless crystals are obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure for Compound 3, (9-phenyl-9H-carbazol-3-yl)boronic acid (1.84 g, 6.41 mmol), 2,2′-dibromo-1,1′-biphenyl (4.00 g, 12.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.296 g, 0.257 mmol), Na2CO3 (2.54 g, 24.0 mmol), H2O (24 mL) and THF (40 mL) yielded Compound 9 (1.69 g, 56%) as a colorless solid after flash chromatography (SiO2, 19:1-hexanes: CH2Cl2): confirmed by LCMS (APCI): calculated for C30H20NBr (M+): 474; Found: 474.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of Compound 2 (3.00 g, 7.57 mmol), 2,2′-dibromo-1,1′-biphenyl (4.72 g, 15.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.350 g, 0.303 mmol), Na2CO3 (3.18 g, 30.0 mmol), H2O (30 mL) and tetrahydrofuran (THF) (50 mL) was degassed with argon for about 44 min while stirring. The reaction mixture was then maintained under argon at about 80° C. while stirring. Upon confirming consumption of the starting material by TLC (SiO2, 19:1-CH2Cl2:acetone), the reaction was cooled to RT and poured over CH2Cl2 (ca. 250 mL). The organics were then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified via flash chromatography (SiO2, 100% CH2Cl2 to 39:1-CH2Cl2:acetone) to yield Compound 3 (2.34 g, 62%) as an off-white foam: confirmed by LCMS (APCI): calculated for C31H21BrN2 (M+): 501; Found: 501. was degassed with argon for about 44 min while stirring consumption of the starting material by TLC (SiO2, 19:1-CH2Cl2:acetone) the reaction was cooled to RT poured over CH2Cl2 (ca. 250 mL) The organics were then washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude product was purified via flash chromatography (SiO2, 100% CH2Cl2 to 39:1-CH2Cl2:acetone)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an atmosphere of argon, 2,2′-dibromobiphenyl (9.5 g, 30 mmole), phenylboronic acid (3.7 g, 30 mmole) and tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.87 mmole, 3% Pd) were dissolved into toluene (75 ml). To the obtained solution, an aqueous solution of sodium carbonate (9.7 g, 92 mmole, 3 eq/46 ml) was added. The resultant solution was heated under refluxing for 10 hours and left standing for one night. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a dark yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane, successively) and a colorless oil (6.5 g, 70%) was obtained. under refluxing for 10 hours left standing for one night The formed organic layer was separated washed with a saturated aqueous solution of sodium chloride (50 ml) dried over anhydrous magnesium sulfate Then, the solvent was removed by distillation a dark yellow oil was obtained The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an atmosphere of argon, 2,2′-dibromobiphenyl (9.5 g, 30 mmole), phenylboronic acid (3.7 g, 30 mmole) and tetrakis(triphenyl-phosphine)palladium(0) (1.0 g, 0.87 mmole, 3% Pd) were dissolved into toluene (75 ml). To the obtained solution, an aqueous solution of sodium carbonate (9.7 g, 92 mmole, 3 eq/46 ml) was added. The resultant solution was heated under refluxing for 10 hours and left standing for one night. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a dark yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane, successively) and a colorless oil (6.5 g, 70%) was obtained. under refluxing for 10 hours left standing for one night The formed organic layer was separated washed with a saturated aqueous solution of sodium chloride (50 ml) dried over anhydrous magnesium sulfate Then, the solvent was removed by distillation a dark yellow oil was obtained The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane