Water → 5-Bromo-2-chloroquinoline

HRID 1492113Notes

Reaction equation

HRID 1492113 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.OS(O)(=O)=O.O.[Br:18]N1C(=O)CCC1=O>[OH-].[Na+]>[Br:18][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([Cl:1])=[N:3]2

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 119282-ChloroquinolineHCID 67184N-bromobutanimide

Product 1

HCID 142210335-Bromo-2-chloroquinolineYield 79%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 2-Chloroquinoline (8) (1.0 g, 6.11 mmol) in 1:1 H2SO4 : H2O (30 ml) was added N-Bromosuccinimide (1.7 g, 9.55 mmol). The mixture was stirred at 35° C. for 38 h and then cooled. The solution was diluted with enough 50% NaOH (aq) to maintain pH<1 and the mixture was extracted with CH2Cl2. The combined organic layers were washed with sat. NaHCO3 (aq) and dried (MgSO4). Concentration of the solvent afforded a dark brown oil (0.078 g, 79%) which was sequentially purified by flash chromatography (85:15 Hexane:CH2Cl2) and MPLC (85:15 Hexane:CH2Cl2) to afford 9 (0.22 g, 15%) as a white amorphous solid (m.p. 71° -72° C.). 1H NMR d (ppm): 7.39 d (CH arom), 7.51 dd (CH arom), 7.74 d (CH arom), 7.91 d (CH atom), 8.37 d (CH arom).

Workup

  1. temperaturecooled
  2. temperatureto maintain pH<1
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organic layers were washed with sat. NaHCO3 (aq)
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-5d326f058aa0422198733ed3c2b3ce39
Source dataset
uspto-grants-1994_12
Patent number
US05372813

Reaction notes

Loading…