N-bromobutanimide → 2-Bromo-6-(bromomethyl)pyridine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.[Br:10]N1C(=O)CCC1=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][Br:10])[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (6-bromopyridin-2-yl)methanol (25 g, 133 mmol) in dichloromethane (200 ml) was charged with triphenylphosphene (41.8 g, 160 mmol). The reaction was cooled to 0° C. and N-bromosuccinimide (26 g, 146 mmol) was added over one minute. After 1 hour, the reaction was concentrated in vacuo and directly purified via silica gel chromatography to afford the title compound.
Workup
- concentrationthe reaction was concentrated in vacuo
- customdirectly purified via silica gel chromatography
Sources & evidence
- ORD record
- ord-8982e3e07ef24f9da2f24877e08aef61
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
Loading…