Acetyl bromide → Ethyl 2-(6-bromopyridin-3-yl)acetate

HRID 546940Notes

Reaction equation

[Br-].[Li+].[C:3]([Br:6])(=O)[CH3:4].[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]1[CH:13]=CC(Cl)=[N:16][CH:17]=1)[CH3:8].[OH-].[Na+]>C(#N)C.O>[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]1[CH:13]=[CH:4][C:3]([Br:6])=[N:16][CH:17]=1)[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

Lithium bromide (3.2 g, 37 mmol) and acetyl bromide (1.3 mL, 17 mmol) were added to a solution of (2-chloro-pyridin-5-yl)acetic acid ethyl ester (1.08 g, 5.42 mmol) in acetonitrile (7.2 mL), and the mixture was heated under reflux at an external temperature of 86 to 94° C. for 31 hours. The reaction mixture was dissolved in water. The solution was neutralized with a sodium hydroxide aqueous solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (655 mg, 53%).

Workup

temperaturethe mixture was heated
extractionfollowed by extraction with diethyl ether
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-1f81d2908373401e962608f5167bc5eb
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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