Pyridine → 2-(4-(5-Bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate

HRID 1175220Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[CH2:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1.N1C=CC=CC=1.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].CC(=O)OCC>C(Cl)Cl.O>[CH3:33][C:32]1[CH:34]=[CH:35][C:29]([S:26]([O:15][CH2:14][CH2:13][O:12][C:11]2[CH:16]=[CH:17][C:8]([CH2:7][C:6]3[CH:18]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[Cl:19])=[CH:9][CH:10]=2)(=[O:28])=[O:27])=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethanol (intermediate I) (3.41 g) in anhydrous DCM (20 mL), pyridine (2.0 eq) was added, and then the mixture was stirred and cooled to 0° C. Then TsCl (1.3 eq) was added in portions, and the mixture was allowed to warmed to room temperature and stirred overnight. TLC (PE:EA=4:1) showed the reaction was complete. Then the mixture was poured into water and extracted with DCM, washed with water and brine, and dried with anhydrous Na2SO4. The solvent was then evaporated under reduced pressure, and the solid crude product was purified by column chromatography (PE:EA=30:1) to obtain intermediate AB (4.05 g, yield 81.7%).

Workup

temperatureto warmed to room temperature
stirringstirred overnight
extractionextracted with DCM
washwashed with water and brine
dry with materialdried with anhydrous Na2SO4
customThe solvent was then evaporated under reduced pressure
customthe solid crude product was purified by column chromatography (PE:EA=30:1)
customto obtain intermediate AB (4.05 g, yield 81.7%)

Sources & evidence

ORD record: ord-b6d8358646d44eb8a76923c9ff08ade8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838499B2

Reaction notes

Loading…