Dimethylformamide → 5-Bromo-2-(3-fluorophenoxy)pyridine

HRID 1891704Notes

Reaction equation

CN(C)C=O.[F:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[H-].[Na+].Br[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1>O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=2)=[N:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an N,N-dimethylformamide (100 mL) solution of 3-fluorophenol (3.30 g, 29.4 mmol) was added sodium hydride (1.41 g, 29.4 mmol, 50% in oil), which was stirred for 10 minutes at 0° C. 2,5-Dibromopyridine (4.64 g, 19.6 mmol) was then added to this mixture at 0° C., followed by 7 hours and 45 minutes of stirring at 110° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (5.81 g, quant.).

Workup

waitfollowed by 7 hours and 45 minutes
stirringof stirring at 110° C
extractionwhich was then extracted with ethyl acetate
customThe organic layer was separated
washwashed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure
customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-fcce0fe24c4348b6a5ddbf5ad7541f82
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507530B2

Reaction notes

Loading…