N-bromobutanimide → 5-broMo-6-fluoroisoquinoline

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).

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

ORD record

ord-9a8d9f1ca58547e49eef9dbbe754a8a9

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073891B2