Azobisisobutyronitrile → 3-(Bromomethyl)-5-nitrobiphenyl

HRID 530382Notes

Reaction equation

C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[CH3:21][C:22]1[CH:23]=[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1>C(Cl)(Cl)(Cl)Cl>[Br:8][CH2:21][C:22]1[CH:23]=[C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

NBS (184 mg, 1.032 mmol) and AIBN (15.4 mg, 0.04 mmol) were added to a solution of 3-methyl-5-nitrobiphenyl (200 mg, 0.938 mmol) in carbon tetrachloride (1.88 mL) and then the reaction mixture was heated to 80° C. for 3 hours. Additional AIBN (15.4 mg, 0.04 mmol) was added to the reaction mixture and was heated for additional 1 hour. The mixture was purified directly by silica gel column chromatography (ethyl acetate/hexanes) to yield 3-(bromomethyl)-5-nitrobiphenyl.

Workup

temperaturewas heated for additional 1 hour
customThe mixture was purified directly by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-97a6d1d6e25a47d7863e2d53a1d0c996
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353066B2

Reaction notes

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