Triethylamine → 2-Bromo-5,6,7,8-tetrahydroquinolin-8-yl methanesulfonate
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:12])[C:4]=2[N:3]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:20][S:21]([O:12][CH:5]1[C:4]2[N:3]=[C:2]([Br:1])[CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=[O:23])=[O:22]Participants
6
Conditions
- Temperature
- 0 °C
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.
Workup
- temperaturewarmed slowly to room temperature
- stirringstirred a further 1 h
- customthe phases were separated
- extractionThe aqueous layer was extracted with CH2Cl2 (3×30 mL)
- dry with materialthe combined organic extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-063d21c295f14515abcd47ec336c942e
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084155B2
Reaction notes
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