Azobisisobutyronitrile → HCID 59013524, compound

Participants

Reaction Steps

3-biphenyl boronic acid (2.0 g, 10 mmol), 3-bromotoluene (1.7 g, 10 mmol), K2CO3 (3.0 g, 21.7 mmol) and Pd(PPh3)4 (100 mg) were refluxed in toluene-H2O (50 mL, 5/1) overnight under N2. Upon extraction with diethyl ether, the crude product was then refluxed overnight with N-bromosuccimide (1.95 g, 11 mmol) and AIBN (100 mg) in anhydrous CCl4 (30 mL). After being washed successively with 5% HCl then 10% NaHCO3, the organic layer was dried and concentrated to give crude 3-(3-phenylphenyl)benzyl bromide as a white powder. This was then reacted following general method C, followed by general method D, affording compound 647 as a pale yellow powder (472 mg, 27% overall yield). Quantative 1H NMR indicated 94% purity. 1H NMR (400 MHz, CDCl3): δ 1.21 (m, 36H, CH3), 2.80 (tt, J=24.8 Hz, 6.8 Hz, 1 H, ArCH2CH), 3.15 (td, J=17.2 Hz, 6.8 Hz, 2H, ArCH2), 5.62-5.69 (m, 8H, POCH2), 7.23-7.85 (m, 13H, aromatic); 31P NMR (162 MHz, CDCl3): 6 20.52.

Provenance & Evidence