(1R,2R)-2-(4-bromophenoxy)cyclopentan-1-ol → trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate
Reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[C@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:9]O[CH2:7]1)(=[O:4])=[O:3].Br[C:20]1C=CC(O[C@@H]2CCC[C@H]2O)=CC=1>>[CH3:1][S:2]([O:5][C@@H:6]1[CH2:7][CH2:20][CH2:9][C@H:10]1[O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=1)(=[O:3])=[O:4]Participants
Procedure
The title compound of Step 2 was prepared according to the general procedure for the synthesis of trans-4-(4-bromophenoxy)tetrahydrofuran-3-yl methanesulfonate in Example 2, except that trans-2-(4-bromophenoxy)cyclopentanol was used in place of trans-4-(4-bromophenoxy)tetrahydrofuran-3-ol, and the reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution. The organic layer was then washed with saturated aqueous ammonium chloride solution, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide product as a brown oil. Yield: 3.86 g, 11.5 mmol, 98%. 1H NMR (400 MHz, CDCl3) δ 1.79-2.00 (m, 4H), 2.14-2.26 (m, 2H), 3.03 (s, 3H), 4.78 (m, 1H), 5.07 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 7.39 (d, J=9.1 Hz, 2H).
Workup
- customthe reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution
- washThe organic layer was then washed with saturated aqueous ammonium chloride solution
- washwashed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto provide product as a brown oil
Sources & evidence
- ORD record
- ord-2957bc1a3a114aceb1161e75ceaf43d1
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278457B2
Reaction notes
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