Potassium Carbonate → 5-((4-Bromo-5-fluoro-2-methoxyphenoxy)methyl)-2-methoxypyridine

HRID 2178342Notes

Reaction equation

[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([O:10][CH3:11])[CH:3]=1.Cl.Cl[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[N:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[N:19][CH:20]=2)=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 4-bromo-5-fluoro-2-methoxyphenol (2.82 g, 12.25 mmol) in N,N-dimethylformamide (50 mL) was added 5-(chloromethyl)-2-methoxypyridine hydrochloride (2.50 g, 12.86 mmol) and potassium carbonate (5.08 g, 36.75 mmol). The reaction mixture was heated to 100° C. After 2 h, the mixture was allowed to cool to room temperature and was diluted with water. The mixture was extracted with ethyl acetate (3×25 mL). The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Chromatographic purification (0-33% ethyl acetate/hexanes elute) afforded 2.76 g (66%) of 5-((4-bromo-5-fluoro-2-methoxyphenoxy)methyl)-2-methoxypyridine as an oil.

Workup

temperatureto cool to room temperature
extractionThe mixture was extracted with ethyl acetate (3×25 mL)
washThe combined organic phases were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customChromatographic purification (0-33% ethyl acetate/hexanes elute)

Sources & evidence

ORD record: ord-84e4e516a7644a02ad5e2b2925c62aeb
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067914B1

Reaction notes

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