Phosphorus oxychloride → 1-(6-Bromo-4-chloroquinolin-3-YL)ethanone

HRID 2271519Notes

Reaction equation

HRID 2271519 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]([C:12](=[O:14])[CH3:13])=[C:5]2O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.P(Cl)(Cl)([Cl:29])=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:14])[CH3:13])=[C:5]2[Cl:29]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 86584982Sodium bicarbonate ethyl acetateHCID 178467072HCID 178467072, compound

Product 1

HCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanoneYield 72%

Conditions

Temperature
85 °C

Procedure

1-(6-Bromo-4-hydroxyquinolin-3-yl)ethanone (2.2 g, 8.27 mmol) was suspended in phosphoryl chloride (30 mL) and the reaction was heated to 85° C. and stirred for 3 h. After this time the reaction mixture was cooled to room temperature and slowly poured into a 2:1 solution of satd. aq. sodium bicarbonate/ethyl acetate that was cooled to 0° C. The organic layer was separated, washed with satd. aq. sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to afford the desired product (710 mg, 72%) as a light brown solid: ESI MS m/z 280 [C11H7BrClNO+H]+.

Workup

  1. temperatureAfter this time the reaction mixture was cooled to room temperature
  2. additionslowly poured into a 2:1 solution of satd
  3. customThe organic layer was separated
  4. washwashed with satd
  5. dry with materialaq. sodium bicarbonate, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-eab596b935c5421c8365147d0006a5d8
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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