Azobisisobutyronitrile → HCID 86644945, compound

HRID 1875177Notes

Reaction equation

[Br:1][C:2]1[C:3]([Cl:20])=[C:4]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.C1C(=O)N([Br:28])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>>[Br:1][C:2]1[C:3]([Cl:20])=[C:4]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:5]([F:9])=[C:6]([CH2:8][Br:28])[CH:7]=1

Participants

Reactant 3

HCID 6547Azobisisobutyronitrile

HCID 67184N-bromobutanimide

HCID 86644946HCID 86644946, compound

Product 1

HCID 86644945HCID 86644945, compoundYield 22%

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-[(3-bromo-2-chloro-6-fluoro-5-methylphenyl)oxy]-5-chlorobenzonitrile (2.74 g, 7.31 mmol) and NBS (1.300 g, 7.31 mmol) in carbon tertrachloride (200 ml) was added AIBN (0.060 g, 0.365 mmol) and the reaction mixture was stirred at 80° C. overnight. The solvent was removed and the crude material was purified via silica gel chromatography to give the title compound 3-{[3-bromo-5-(bromomethyl)-2-chloro-6-fluorophenyl]oxy}-5-chlorobenzonitrile (1.04 g, 1.604 mmol, 22% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.01 (d, 1H), 7.79 (s, 1H), 7.58 (s, 2H), 4.68 (s, 2H)

Workup

customThe solvent was removed
customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record: ord-f970d95408df40d6b6942ba58d7f6768
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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