Carbon tetrabromide → 3-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

HRID 2101406Notes

Reaction equation

O[CH2:2][C:3]1[C:4]([CH3:14])=[N+:5]([O-:13])[C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:2][C:3]1[C:4]([CH3:14])=[N+:5]([O-:13])[C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 3-(hydroxymethyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide (207 mg, 1.0 mmol) and carbon tetrabromide (400 mg, 1.2 mmol) in CH2Cl2 (5 mL) at 0° C. was added Ph3P (393 mg, 1.5 mmol) in small portions over 5 min. The reaction mixture was then stirred at 0° C. for 30 min. Analysis by HPLC/MS indicated the reaction was complete. The reaction mixture was directly loaded onto a silica gel cartridge (40 g) and eluted with a gradient of EtOAc (0-100%) in hexanes to afford 202 mg (75%) of the title compound as a white solid. HPLC/MS: retention time=2.10 min, [M+H]+=269.9.

Workup

washeluted with a gradient of EtOAc (0-100%) in hexanes

Sources & evidence

ORD record: ord-2b1bb049e77843c89145f0bcedffb224
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Reaction notes

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