Benzoyl Peroxide → Methyl 3-(bromomethyl)-4'-nitrobiphenyl-4-carboxylate

HRID 403860Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:46])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:46][CH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

The compound of example 220 (5 g, 0.0184 mol) was dissolved in carbon tetrachloride (125 mL). Benzoyl peroxide (250 mg) and NBS (3.6 g, 0.0202 mol) were added and the reaction mixture was refluxed at 80° C. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated to yield crude residue containing 85% mono bromo and 10% dibromo product and 5% starting material. The crude title compound obtained was used directly for preparation of compound of example 222.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through celite
concentrationThe filtrate was concentrated
customto yield crude residue
additioncontaining 85% mono bromo and 10% dibromo product and 5%

Sources & evidence

ORD record: ord-a6f066b724b1453785be9275f7a10f9e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748426B2

Reaction notes

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