Benzoyl Peroxide → 6-Bromomethyl-3-methoxy-2-(3-trifluoromethyl-phenyl)-pyridine

HRID 1632015Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C1C(=O)N([Br:27])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:9][C:6]1[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the 3-methoxy-6-methyl-2-(3-trifluoromethyl-phenyl)-pyridine synthesized above (1.3 g, 4.86 mmol) and NBS (1.04 g, 5.83 mmol) in CCl4 (25 mL) was added benzoyl peroxide (0.12 g, 0.49 mmol). The reaction was stirred at 80° C. under N2 for 20 h. The reaction was cooled to room temperature and concentrated. The residue was dissolved in mixture of dichloromethane and hexanes (1:1, 8 mL) and purified by silica gel column chromatography using 1:1 dichloromethane-hexanes to afford 0.74 g (44%) of 6-bromomethyl-3-methoxy-2-(3-trifluoromethyl-phenyl)-pyridine as off-white solid.

Workup

temperatureThe reaction was cooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in mixture of dichloromethane and hexanes (1:1, 8 mL)
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-e9477196ffb54825b60ebb98b1696d32
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791267B2

Reaction notes

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