Sulfuric Acid → 8-Bromo-6-fluoroquinoline

HRID 1178790Notes

Reaction equation

HRID 1178790 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Na+].[N+]([C:14]1[CH:15]=C(S([O-])(=O)=O)C=C[CH:19]=1)([O-])=O.S(=O)(=O)(O)O.[OH-].[Na+]>OCC(CO)O>[F:9][C:7]1[CH:6]=[C:5]2[C:3](=[C:2]([Br:1])[CH:8]=1)[N:4]=[CH:15][CH:14]=[CH:19]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 2428732-Bromo-4-fluoroaniline

Product 1

HCID 212712498-Bromo-6-fluoroquinolineYield 416.7%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 7.0 g of 2-bromo-4-fluoro-aniline, 7.0 g of glycerol and 13.0 g of m-nitrobenzene sulfonic acid sodium salt, 20 ml of 70% sulfuric acid was added drop by drop. The reaction temperature was raised to 150° C. for 4 hr. The mixture was cooled, poured on water neutralized with NaOH and the formed precipitate was filtered to yield 34.7 g of 6-fluoro-8-bromo-quinoline. MS (ES) m/z (relative intensity): 227 (M++H, 100).

Workup

  1. additionwas added drop by drop
  2. temperatureThe mixture was cooled
  3. additionpoured on water
  4. filtrationthe formed precipitate was filtered

Sources & evidence

ORD record
ord-8195d11e4aab4041a7fd5e609d76dbfb
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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