Boron tribromide → 7-Isoquinolinol

HRID 275024

Reaction equation

HRID 275024 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 5943757-Methoxyisoquinoline

Product 1

HCID 4597677-IsoquinolinolYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-75 °C

Procedure

To a 2-liter, 3-necked round bottom flask equipped with a magnetic stir bar and addition funnel is added 19.7 g (0.124 mole) 7-methoxyisoquinoline and 800 ml of dry dichloromethane. This solution is stirred and cooled to -75° C. with a dry ice/acetone bath, 628 ml (0.628 mole) of 1.0M boron tribromide in dichloromethane is added dropwise maintaining the temperature at -75° C. Thereafter the slurry is stirred for 18 hours allowing the temperature to rise to room temperature. The reaction slurry is poured into 1 liter of ice water and stirred for an hour. The layers are separated and the aqueous layer is then adjusted from acidic to neutral (pH 7) with 1N NaOH. A yellow solid precipitates and is filtered off, then air dried to yield 14.5 g of a yellow solid, 81%.

Workup

  1. customTo a 2-liter, 3-necked round bottom flask equipped with a magnetic stir bar and addition funnel
  2. temperaturemaintaining the temperature at -75° C
  3. stirringThereafter the slurry is stirred for 18 hours
  4. customto rise to room temperature
  5. stirringstirred for an hour
  6. customThe layers are separated
  7. customA yellow solid precipitates
  8. filtrationis filtered off
  9. customair dried

Sources & evidence

ORD record
ord-2eb021ee90314686978be7b90848b164
Source dataset
uspto-grants-1995_02
Patent number
US05391743

Linked notes

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