N-bromobutanimide → 3-Bromo-2-fluoro-6-(neopentyloxy)pyridine

HRID 455696

Reaction equation

[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:11]=1>C(#N)C>[Br:1][C:15]1[C:10]([F:9])=[N:11][C:12]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-bromosuccinimide (8.29 g, 46.6 mmol) was added to a solution of 2-fluoro-6-(neopentyloxy)pyridine (7.11 g, 38.8 mmol) in acetonitrile (80 mL) at rt. The reaction mixture was heated to 70° C. overnight. The reaction mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was dissolved in DCM and washed with water. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (100% hexanes) to obtain 3-bromo-2-fluoro-6-(neopentyloxy)pyridine (5.27 g, 20.11 mmol) as a white solid.

Workup

temperatureThe reaction mixture was cooled to rt
customthe solvent was removed under reduced pressure
dissolutionThe residue was dissolved in DCM
washwashed with water
customThe organic layer was separated
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (100% hexanes)

Sources & evidence

ORD record: ord-4d5c88843d5f4cb193de66352cd81375
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Linked notes

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