Phosphorus oxychloride → 1-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one

HRID 2271514노트

반응식

HRID 2271514 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.P(Cl)(Cl)([Cl:31])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2[Cl:31]

참가 물질

4

반응물 3

HCID 24813Phosphorus oxychlorideHCID 86584982Sodium bicarbonate ethyl acetateHCID 178450272HCID 178450272, 화합물

생성물 1

HCID 680919931-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one수율 89%

반응 조건

온도
85 °C

실험 절차

1-(6-Bromo-4-hydroxyquinolin-3-yl)-2-methylpropan-1-one (16.0 g, 54.4 mmol) was added to phosphoryl chloride (160 mL) and the reaction was stirred at 85° C. for 1.5 h. The reaction mixture was cooled and slowly poured into a 2:1 solution of satd. aq. sodium bicarbonate/ethyl acetate at 0° C. The organic layer was separated and was washed with satd. aq. sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (14.8 g, 89%) as a yellow solid: ESI MS m/z 312 [C13H11BrClNO+H]+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. additionslowly poured into a 2:1 solution of satd
  3. customat 0° C
  4. customThe organic layer was separated
  5. washwas washed with satd
  6. dry with materialaq. sodium bicarbonate and brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f569a67eaae148e2ab98e47ffeeb9d99
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120749B2

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