N-bromobutanimide → 5-broMo-6-fluoroisoquinoline

HRID 2098110Notes

Reaction equation

HRID 2098110 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.C1C(=O)N([Br:19])C(=O)C1>OS(O)(=O)=O>[Br:19][C:3]1[C:2]([F:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 218898476-Fluoroisoquinoline

Product 1

HCID 687577385-broMo-6-fluoroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirring mixture of 6-fluoroisoquinoline in H2SO4 (5 mL) at 0° C. was added solid NBS (1.5 EQ) slowly over 5 min. The reaction mixture was reacted at 0° C. for 1 h. To this reaction mixture was added NBS (0.5 EQ). The cold bath was then removed. The reaction mixture was reacted until all the starting material was consumed. To this reaction mixture was neutralized with a cold solution of NaOH (5N) until the pH of this mixture >10. The white solid was filtered off and dissolved in DCM and washed with a solution of NaOH (1N). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified via a column to give 5-bromo-6-fluoroisoquinoline. Retention time (min)=2.810, method [3], MS (ESI) 226.0 (M+H).

Workup

  1. customThe reaction mixture was reacted at 0° C. for 1 h
  2. customThe cold bath was then removed
  3. customThe reaction mixture was reacted until all the starting material
  4. customwas consumed
  5. filtrationThe white solid was filtered off
  6. dissolutiondissolved in DCM
  7. washwashed with a solution of NaOH (1N)
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified via a column

Sources & evidence

ORD record
ord-4c0ae78df0f1477d8239c044680fd089
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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