Phosphorus oxychloride → 6-Bromo-4-chloro-3-(methylsulfonyl)quinoline
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2O.P(Cl)(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[Cl:19]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
6-Bromo-3-(methylsulfonyl)quinolin-4-ol (573 mg, 1.90 mmol) was added to phosphoryl chloride (19 mL) and the reaction was stirred at 100° C. 16 h. Additional THF (5 mL) was added and the reaction mixture was stirred at 100° C. for 4 h. The reaction mixture was cooled and slowly poured into a 2:1 solution of satd. aq sodium bicarbonate/ethyl acetate that was pre-cooled to 0° C. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with satd. aq.sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (360 mg, 59%) as a white solid: ESI MS m/z 321 [C10H7BrClNO2S+H]+.
Workup
- custom16 h
- stirringthe reaction mixture was stirred at 100° C. for 4 h
- temperatureThe reaction mixture was cooled
- additionslowly poured into a 2:1 solution of satd
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe combined organic layers were washed with satd
- dry with materialsodium bicarbonate, dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e820920cb8ea4ce69daa5adcf6cebc3c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
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