3-Hydroxy-2-nitropyridine → 6-Bromo-2-nitropyridin-3-ol

HRID 2233330Notes

Reaction equation

[OH:1][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O>CN(C=O)C>[Br:11][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N+:8]([O-:10])=[O:9])[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Hydroxy-2-nitropyridine (100 g, 0.714 mole) was dissolved in DMF (1 L), the solution was cooled to 0° C., and N-bromosuccinimide (165 g, 0.927 mole) was added portionwise over 5 hr. The mixture was then stirred at RT for 15 hr and concentrated in vacuo. The residue was taken up in Et2O (500 mL) and the mixture was stirred for 30 min. The precipitate was removed by suction filtration, and the filtrate was concentrated in vacuo to afford the title compound (180 g): MS (ES) m/e 219.0 (M+H)+. This material was used without further purification.

Workup

concentrationconcentrated in vacuo
stirringthe mixture was stirred for 30 min
customThe precipitate was removed by suction filtration
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-6cddd407577c4faba58760f0f8bfd593
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709496B2

Reaction notes

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