Reaction #1458438

Reaction equation

2-bromoethanol

5,7-dibromo-8-hydroxyquinoline

2-bromoethanol

2-bromoethanol

dimethylformamide

→

5,7-dibromo-8-(2-hydroxyethyl)quinoline

Yield 76.9%

Solvents

water

Conditions

Workup

1. 1
   workup.STIRRINGwhile stirring
2. 2
   FiltrationThe precipitated product was collected by filtration
3. 3
   Washwashed with 50 mL of 0.5 M aqueous potassium carbonate, plain water and air
4. 4
   Otherdried
5. 5
   WashThe solid was washed through the funnel
6. 6
   workup.DISSOLUTIONby dissolving in dichloromethane
7. 7
   Otherthe solvent was removed

Procedure

A solution of 3.79 g of 5,7-dibromo-8-hydroxyquinoline (12.5 mmol) and 975 mL of 2-bromoethanol (13.75 mmol) in 20 mL of dry dimethylformamide containing 5.18 g anhydrous potassium carbonate (37.5 mmol) was placed under argon atmosphere and heated at 60° C. with vigorous magnetic stirring. After 4 hr a further 220 μL of 2-bromoethanol was added and stirring continued at 60° overnight. After 22 hr another 440 μL of 2-bromoethanol was added. After 4 days the mixture was poured into 150 mL of water while stirring. The precipitated product was collected by filtration, washed with 50 mL of 0.5 M aqueous potassium carbonate, plain water and air dried. The solid was washed through the funnel by dissolving in dichloromethane, and the solvent was removed to yield 3.18 g of 5,7-dibromo-8-(2-hydroxyethyl)quinoline. After recrystallization from methanol/water containing a little triethylamine, the melting point was 128–131° C.

Source