Phosphorus tribromide → 6-(Bromomethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine

HRID 709644Notes

Reaction equation

P(Br)(Br)[Br:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:25]O)=[N:18][C:19]=1[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:2][CH2:25][C:17]1[N:18]=[C:19]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([C:7]2[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=2[F:5])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Phosphorus tribromide (112 μL) was added to DMF (3.0 mL) at 0° C., and the mixture was stirred at 0° C. for 20 min. To the obtained white suspension was added a solution of (5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol (300 mg) in DMF (1.0 mL), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (255 mg) as a pale-yellow oil.

Workup

stirringthe mixture was stirred at room temperature for 1 hr
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-fe194895c1e942f6a3c5d57cb38782dd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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