Reaction #7228

Reaction equation

NaHCO3

triethylamine

2-bromo-5,6,7,8-tetrahydroquinolin-8-ol

methanesulfonyl chloride

→

2-bromo-5,6,7,8-tetrahydroquinolin-8-yl methanesulfonate

Yield 88.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Temperaturewarmed slowly to room temperature
2. 2
   workup.STIRRINGstirred a further 1 h
3. 3
   Otherthe phases were separated
4. 4
   ExtractionThe aqueous layer was extracted with CH2Cl2 (3×30 mL)
5. 5
   Dryingthe combined organic extracts were dried (MgSO4)
6. 6
   Concentrationconcentrated

Procedure

To a cold (0° C.) stirred solution of 2-bromo-5,6,7,8-tetrahydroquinolin-8-ol (500 mg, 2.36 mmol) in dry CH2Cl2 (10 mL) was added triethylamine (0.72 mL, 5.2 mmol) followed by methanesulfonyl chloride (0.35 mL, 3.6 mmol). The resulting mixture was stirred at 0° C. for 1 h, then warmed slowly to room temperature and stirred a further 1 h. Saturated aqueous NaHCO3 (30 mL) was added and the phases were separated. The aqueous layer was extracted with CH2Cl2 (3×30 mL) and the combined organic extracts were dried (MgSO4) and concentrated to give 605 mg (88%) of 2-bromo-5,6,7,8-tetrahydroquinolin-8-yl methanesulfonate as an orange solid.

Source