Phosphorus oxychloride → 1,7-Dichloro-6-fluoroisoquinoline
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-])=[CH:9]2)=[CH:4][C:3]=1[F:13].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:9]1[C:10]2[C:5](=[CH:4][C:3]([F:13])=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1Participants
3
Procedure
2.6 g (12.0 mmol) of 7-chloro-6-fluoro-isoquinoline 2-oxide (5) were heated in 40 ml of POCl3 at reflux for 4 h. After the mixture has cooled down to room temperature, it was poured on ice. The aqueous solution was extracted three times with dichloromethane. The combined organic layers were dried with magnesium sulfate and evaporated to yield 2.91 g of the title compound, which was used without further purification. Rt=2.34 min (Method A). Detected mass: 216.0/218.0 (M+H+).
Workup
- temperatureat reflux for 4 h
- additionit was poured on ice
- extractionThe aqueous solution was extracted three times with dichloromethane
- dry with materialThe combined organic layers were dried with magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-85de4847ebec470081e2330141a64a29
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609691B2
Reaction notes
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