Sulfuric Acid → 8-Bromo-6-fluoroquinoline

HRID 2241967Notes

Reaction equation

HRID 2241967 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>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

5

Reactant 3

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

Product 1

HCID 212712498-Bromo-6-fluoroquinoline

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-bromo-4-fluoroaniline (commercially available, 7.0 g), glycerol (7.0 g) and m-nitrobenzene sulfonic acid sodium salt (13.0 g) was added 20 ml of 70% sulfuric acid dropwise. The reaction temperature was raised to 150° C. for 4 hr. The mixture then was cooled to room temperature, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and the resulting precipitate was collected by vacuum filtration to yield 3.47 g of the title compound as a light yellow solid; MP=75-78° C.; MS (ES) m/z (relative intensity): 227 (M+H)+ (100).

Workup

  1. temperatureThe mixture then was cooled to room temperature
  2. additionpoured on ice water
  3. filtrationfiltered through celite
  4. filtrationthe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-500f8066cb2c47ef9fd74241f1596944
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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