Azobisisobutyronitrile → 2-[(3-Bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene

HRID 1875146Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:15]([F:16])=[C:14]([CH3:17])[CH:13]=[CH:12][C:11]=2[Cl:18])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:15]([F:16])=[C:14]([CH2:17][Br:26])[CH:13]=[CH:12][C:11]=2[Cl:18])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[(3-bromo-5-chlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (9.69 g, 27.7 mmol) and NBS (4.93 g, 27.7 mmol) in carbon tetrachloride (250 ml) was added AIBN (0.227 g, 1.384 mmol) and the mixture was stirred at 80° C. overnight. An additional portion of AIBN (0.227 g, 1.384 mmol) was added and the mixture was stirred for another 4 hours. The mixture was cooled to rt, the solvent was removed and the crude material was purified via silica gel chromatography to give 2-[(3-bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (5.78 g, 49% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.38-7.67 (m, 3H), 7.10 (s, 1H), 6.98-7.07 (m, 1H), 4.70 (s, 2H)

Workup

stirringthe mixture was stirred for another 4 hours
temperatureThe mixture was cooled to rt
customthe solvent was removed
customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record: ord-35b6b1cdcccb4a74a084b82047f071d0
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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