Phosphorus oxychloride → 8-Bromo-4-chloro-2-methylquinoline

HRID 1700113Notes

Reaction equation

HRID 1700113 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:16])=O>>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:16])[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 178428808HCID 178428808, compound

Product 1

HCID 7684838-Bromo-4-chloro-2-methylquinolineYield 97%

Conditions

Temperature
100 °C

Procedure

Part A: To a quantity of 4.76 g (20 mmol) of 2-methyl-4-hydroxy-8-bromo-quinoline (J.Org.Chem. 1964, pg 3548) 15 ml of phosphorous oxychloride was added under ice-cooling. After heating to 100° C. for 30 minutes and subsequent cooling residual phosphorous oxychloride was removed by evaporation. After addition of ice water to the residue the mixture was neutralized with ammonia and extracted with CH2Cl2. The organic layer was dried over magnesium sulphate and concentrated in vacuo. The resulting product was purified on a silicagel column using ethylacetate as eluent. A total of 5.0 g of 2-methyl-4-chloro-8-bromo-quinoline was obtained (97% yield)

Workup

  1. temperaturecooling
  2. customwas removed by evaporation
  3. additionAfter addition of ice water to the residue the mixture
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting product was purified on a silicagel column

Sources & evidence

ORD record
ord-70289fe802a84213abf80a354fa905cc
Source dataset
uspto-grants-2002_02
Patent number
US06350750B1

Reaction notes

Loading…