Phosphorus oxybromide → HCID 11345640, compound
Reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10](OCC)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:19])=O>>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:19])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 135 °C
Procedure
One hundred fifteen g. of 2-benzyl-6-ethoxypyridine and 200 g. of phosphorous oxybromide were heated together with stirring at 135°C. for 1 hour. The mixture gave off a gas during the first 15 minutes of the reaction but remained calm for the rest of the heating period. On cooling, the mixture became an intractable tar and the reaction flask was broken to obtain the crude product. It was partitioned between 2 liters of water, 270 ml. of 10N sodium hydroxide solution and 1 liter of chloroform. The organic extract was washed with 1 liter of water and dried over magnesium sulfate. Removal of the desiccant and solvent yielded a dark oil which was extracted with 750 ml. of petroleum ether (b.p. 60°-80°C.), and treated with decolorizing charcoal. Removal of the solids and solvent yielded the product as an amber oil. This material was used without further purification for the next step.
Workup
- customThe mixture gave off a gas
- customduring the first 15 minutes of the reaction
- temperatureOn cooling
- customto obtain the crude product
- customIt was partitioned between 2 liters of water, 270 ml
- extractionThe organic extract
- washwas washed with 1 liter of water
- dry with materialdried over magnesium sulfate
- customRemoval of the desiccant and solvent
- customyielded a dark oil which
- extractionwas extracted with 750 ml
- additionof petroleum ether (b.p. 60°-80°C.), and treated with decolorizing charcoal
- customRemoval of the solids and solvent
Sources & evidence
- ORD record
- ord-a076f7c84568425f9dcdae09b59a47e9
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03941796
Reaction notes
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