trans-2-(4-Bromophenoxy)cyclohexanol → (1R,2R)-2-(4-bromophenoxy)cyclohexyl methanesulfonate

HRID 2060841Notes

Reaction equation

HRID 2060841 reaction equation
[CH3:1][S:2]([O:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=[O:4])=[O:3].Br[C:20]1C=CC(O[C@@H]2CCCC[C@H]2O)=CC=1>>[CH3:1][S:2]([O:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][CH2:20][C@H:7]1[O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 67195202trans-2-(4-Bromophenoxy)cyclohexanolHCID 86653037trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate

Product 1

HCID 86653049(1R,2R)-2-(4-bromophenoxy)cyclohexyl methanesulfonate

Procedure

The title compound of Step 4 was prepared according to the general procedure for the synthesis of trans-2-(4-bromophenoxy)cyclopentyl methanesulfonate in Example 5, except that (1R,2R)-2-(4-bromophenoxy)cyclohexanol was used instead of trans-2-(4-bromophenoxy)cyclopentanol. (1R,2R)-2-(4-bromophenoxy)cyclohexyl methanesulfonate was obtained as a light golden oil. Yield: 3.60 g, 10.3 mmol, quantitative. 1H NMR (400 MHz, CDCl3) δ 1.26-1.51 (m, 3H), 1.64-1.84 (m, 3H), 2.19 (m, 1H), 2.30 (m, 1H), 2.97 (s, 3H), 4.22 (ddd, J=10.2, 8.5, 4.6 Hz, 1H), 4.64 (ddd, J=10.6, 8.4, 4.9 Hz, 1H), 6.82 (d, J=9.1 Hz, 2H), 7.39 (d, J=9.1 Hz, 2H).

Workup

  1. customThe title compound of Step 4 was prepared

Sources & evidence

ORD record
ord-677a5e1730d44f50b38ccc257f3c2934
Source dataset
uspto-grants-2012_10
Patent number
US08278457B2

Reaction notes

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