Water → 2-(Cyclopropyloxy)-5-(trifluoromethoxy)phenylmethyl Methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]1([O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[CH2:21][OH:22])[CH2:8][CH2:7]1.C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:22][CH2:21][C:11]1[CH:12]=[C:13]([O:16][C:17]([F:19])([F:20])[F:18])[CH:14]=[CH:15][C:10]=1[O:9][CH:6]1[CH2:7][CH2:8]1)(=[O:4])=[O:3]Participants
Conditions
- Temperature
- 0 °C
Procedure
Methanesulfonyl chloride (0.31 mL, 0.46 g, 4.0 mmol) was added dropwise to a stirred, cooled (−10° C.) solution of 2-(cyclopropyloxy)-5-(trifluoromethoxy)benzenemethanol (WO9900368, 0.5 g, 2.0 mmol) and triethylamine (0.56 mL, 0.40 g, 4.0 mmol) in dichloromethane (10 mL) and the mixture was stirred at 0° C. for 30 minutes, then at room temperature for 2 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with aqueous citric acid (10%, 20 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.28-7.22 (3H, m), 5.20 (2H, s), 3.80-3.77 (1H, m), 3.01 (3H, s), and 0.85-0.79 (4H, m).
Workup
- waitat room temperature for 2 hours
- extractionthe mixture was extracted with ethyl acetate (2×50 mL)
- washThe combined organic fractions were washed with aqueous citric acid (10%, 20 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL)
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-77e5e1251b8f4eb1ad3e74ff81d869f1
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06953792B2
Reaction notes
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