Azobisisobutyronitrile → Methyl 4-(bromomethyl)-4'-nitrobiphenyl-3-carboxylate

HRID 403698

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:17]([O:19][CH3:20])=[O:18].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:40])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:40][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

The compound of example 3 (5.7 g, 0.021 mol) was dissolved in carbon tetrachloride (125 mL). AIBN (350 mg) and NBS (4.1 g, 0.0231 mol) were added and the reaction mixture was refluxed at 80° C. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated to obtain a crude material containing 85% mono bromo and 10% dibromo product and 5% starting material. The crude was used directly without purification for the preparation of the compound of example 5.

Workup

customAfter completion of the reaction
temperaturethe reaction mixture was cooled to room temperature
filtrationfiltered through celite
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-7566dc0364ba4d0e8bd6b284ae59ec52
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748426B2

Linked notes

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