반응 #7228

반응 방정식

NaHCO3

triethylamine

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

methanesulfonyl chloride

→

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

수율 88.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도warmed slowly to room temperature
2. 2
   workup.STIRRINGstirred a further 1 h
3. 3
   기타the phases were separated
4. 4
   추출The aqueous layer was extracted with CH2Cl2 (3×30 mL)
5. 5
   건조the combined organic extracts were dried (MgSO4)
6. 6
   농축concentrated

실험 절차

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.

출처