synthesis

Carry out all catalytic reactions in reaction vessels open to the air. Charge a round-bottom flask with the newly purchased or freshly recrystallized aryl boronic acid (2.0 mmol), 1,2-dibromobenzene, powdered K3PO4 (2.2 mmol) and toluene (2.5 mL) of technical quality. Stir the mixture vigorously. Heat the mixture to 80 °C for 10 minutes. Add (0.2 mol%) of catalyst by syringe as a 2.5 ml of toluene solution to the mixture. Take the samples periodically from the reaction mixture. Quench the reaction with water. Extract the mixture with ethyl acetate. Analyze the reaction by GC-MS. At the end of catalytic reaction, cool the reaction mixture to room temperature. Quench the mixture with water (adjusted to an appropriate pH when biaryls with acidic or basic groups has to be extracted). Extract the mixture with ethyl acetate (3×40 mL). Dry the combined extracts (MgSO4). Evaporate the combined extracts to dryness. Purify the crude material by flash chromatography on silica gel.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 3037, 1979 DOI: 10.1021/jo01331a016Tetrahedron Letters, 21, p. 845, 1980 DOI: 10.1016/S0040-4039(00)71521-8

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Bromobiphenyl is sensitive to light. Low reactivity.

Fire Hazard

Flash point data for 2-Bromobiphenyl are not available. 2-Bromobiphenyl is probably combustible.

Physical properties

2-Bromobiphenyl has a melting point of 1.5-2 °C, so it is a colorless liquid at room temperature. It boils at 297-298 °C. Its density at 25℃ is 1.352 g/mL. In general, 2-bromobiphenyls are stable, but they are not compatible with oxidants.

General Description

Clear liquid. Insoluble in water.