Reaction #684969

Reaction equation

Water

ethyl acetate

1-hydroxyisoquinoline

Bromine

→

title compound

Yield 80.1%

4-Bromo-1-isoquinolinol

Yield 80.1%

Solvents

tetrahydrofuran

acetic acid

Conditions

Workup

1. 1
   Otherthe resulting reaction mixture
2. 2
   Filtrationwas filtered
3. 3
   Filtrationthrough filter paper
4. 4
   WashThe organic layer was washed with saturated brine
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was recrystallized from ethyl acetate and hexane

Procedure

Bromine (1.78 ml, 34.5 mmol) was added to an ice-cooled solution of 1-hydroxyisoquinoline (5.01 g, 34.5 mmol) in acetic acid (50 ml), and this reaction mixture was stirred at room temperature for 2 hours. Water, ethyl acetate, and tetrahydrofuran were added, and the resulting reaction mixture was filtered through filter paper. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate and hexane to give the title compound (6.19 g).

Source