Phosphorus oxychloride → 3,5-Dibromo-4-chloropyridine
Reaction equation
[Br:1][C:2]1[C:7](=O)[C:6]([Br:9])=[CH:5][NH:4][CH:3]=1.P(Cl)(Cl)([Cl:12])=O.C(=O)([O-])O.[Na+]>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[Cl:12]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
To 3,5-dibromo-4-(1H)-pyridone (W, 1.0 g, 3.97 mmol) was added phosphorous oxychloride (5 mL) and the mixture was heated at 100° C. for 2 h. The mixture was poured into ice/water (25 g) and basified by the addition of a saturated solution of sodium hydrogen carbonate. The mixture was extracted with dichloromethane (2×20 mL), the combined organic extracts were washed with saturated aqueous sodium chloride solution (25 mL), dried over sodium sulphate and concentrated under vacuum to obtain the title compound. MS (M+1): 271.8.
Workup
- extractionThe mixture was extracted with dichloromethane (2×20 mL)
- washthe combined organic extracts were washed with saturated aqueous sodium chloride solution (25 mL)
- dry with materialdried over sodium sulphate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-ba475e0f78b6437b872ba3c46c2267d6
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073929B2
Reaction notes
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