Azobisisobutyronitrile → 3-(6-Bromo-3-bromomethyl-2-fluoro-phenoxy)-5-chloro-benzonitrile

HRID 1875080Notes

Reaction equation

[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH3:19])=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH2:19][Br:27])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-[(6-bromo-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile (8.1 g, 23.78 mmol), NBS (5.08 g, 28.5 mmol) and AIBN (0.195 g, 1.189 mmol) in CCl4 (240 ml) was heated at 90° C. for 16 h under an atmosphere of nitrogen. The mixture was cooled to 0° C., filtered thru Celite and concentrated. The crude yellow oil was purified on silica gel (hexanes/ethyl acetate) to give 2.75 g (26%) of 3-{[6-bromo-3-(bromomethyl)-2-fluorophenyl]oxy}-5-chlorobenzonitrile as a clear oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.44 (dd, 1H), 7.34 (t, 1H), 7.18-7.32 (m, 1H), 7.13 (t, 1H), 6.89-7.05 (m, 1H), 4.45 (d, 2H).

Workup

temperatureThe mixture was cooled to 0° C.
filtrationfiltered
concentrationconcentrated
customThe crude yellow oil was purified on silica gel (hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-df445502d4f84430b09c1302a2c6c144
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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