Benzoyl Peroxide → Bromobenzyl Cyanide

To a solution of benzyl cyanide (4.93 mL, 42.7 mmol) in CCl4 (275 mL) were added dibenzoyl peroxide (517 mg, 2.13 mmol) and N-bromosuccinimide (9.12 g, 51.2 mmol). The reaction mixture was heated to reflux and stirred for 5 hours and concentrated in vacuo to a volume of 100 mL. The solution was partitioned between CHCl3 and saturated NaHCO3 solution, and the aqueous layer was extracted with several portions of CHCl3. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford a yellow oil. Purification was achieved by flash column chromatography on silica gel using a gradient elution of 0-20% EtOAc/hexanes. Collection and concentration of the appropriate fractions yielded the title compound as a pale yellow oil. 1H NMR (400 MHz, d6-DMSO) δ 7.61-7.58 (m, 2H), 7.53-7.45 (m, 3H), 6.59 (s, 1H).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux
3. concentrationconcentrated in vacuo to a volume of 100 mL
4. customThe solution was partitioned between CHCl3 and saturated NaHCO3 solution
5. extractionthe aqueous layer was extracted with several portions of CHCl3
6. dry with materialThe combined organic layers were dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customto afford a yellow oil
9. customPurification
10. washa gradient elution of 0-20% EtOAc/hexanes
11. customCollection and concentration of the appropriate fractions

ORD record

ord-6cd50916e47b4bbba89d2919297ee175

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476666B2