Bromobenzene → Biphenyl

HRID 2175735Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of bromobenzene (0.079 g, 0.5 mmol), phenyl boronic acid (0.073 g, 0.60 mmol) and potassium carbonate (0.138 g, 1 mmol) in 1,4-dioxane solvent (2.0 mL) was added the solid catalyst (0.01 mmol, 2 mol %) under argon gas. The reaction was then stirred at 80° C. for 16 hours. The mixture was then cooled to room temperature, filtered and concentrated in vacuo. The residue was subsequently purified by silica gel chromatography (hexanes/EtOAc or hexanes/ether). The isolated product was characterized by 1H NMR spectroscopy. Characterization Data (Biphenyl): Isolated as colorless solid; 1H NMR (CDCl3, 300 MHz): δ 7.71 (4H, d, J=7.8 Hz), 7.55 (4H, t, J=7.5 Hz), 7.45 (2H, t, J=7.2 Hz). Results are shown in Table 4.

Workup

temperatureThe mixture was then cooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was subsequently purified by silica gel chromatography (hexanes/EtOAc or hexanes/ether)

Sources & evidence

ORD record: ord-0406b5d676b3425a80a22fb5919a59bf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062085B2

Reaction notes

Loading…