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

HRID 2038467Notes

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-9b001fb3e1d9475398149a84ff3c1560
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575321B2

Reaction notes

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