Phosphorus oxychloride → 6-Bromo-4-chloro-3-(methylsulfonyl)quinoline

HRID 2271517ノート

反応式

HRID 2271517 の反応式
[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]

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 86584982Sodium bicarbonate ethyl acetateHCID 178504827HCID 178504827、化合物

生成物 1

HCID 667152456-Bromo-4-chloro-3-(methylsulfonyl)quinoline収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  1. custom16 h
  2. stirringthe reaction mixture was stirred at 100° C. for 4 h
  3. temperatureThe reaction mixture was cooled
  4. additionslowly poured into a 2:1 solution of satd
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with satd
  8. dry with materialsodium bicarbonate, dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-e820920cb8ea4ce69daa5adcf6cebc3c
出典データセット
uspto-grants-2015_09
特許番号
US09120749B2

反応ノート

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