Diethyl Ether → 2-[4-(3,5-Difluorophenoxy)phenoxy]ethyl p-toluenesulfonate

HRID 1638310Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[O:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(OCC)C>N1C=CC=CC=1>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:13][CH2:12][CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]3[CH:3]=[C:2]([F:1])[CH:18]=[C:17]([F:19])[CH:16]=3)=[CH:15][CH:14]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2-[4-(3,5-difluorophenoxy)phenoxy]ethanol (2.66 g, 10.0 mmol) in pyridine (2.8 g), p-toluenesulfonyl chloride (1.91 g, 10.0 mmol) was gradually added with stirring while cooling at -20° C., and the resultant mixture was allowed to stand in a refrigerator overnight. Diethyl ether was added to the reaction mixture, which was washed with dilute hydrochloric acid until the aqueous layer became acidic, followed by washing with an aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The obtained ether layer was dried over anhydrous magnesium sulfate, and the solvent was removed to give 2-[4-(3,5-difluorophenoxy)phenoxy]ethyl p-toluenesulfonate (3.90 g).

Workup

customto stand in a refrigerator overnight
washwas washed with dilute hydrochloric acid until the aqueous layer
washby washing with an aqueous sodium bicarbonate solution
dry with materialThe obtained ether layer was dried over anhydrous magnesium sulfate
customthe solvent was removed

Sources & evidence

ORD record: ord-7824e3c998dd4fa882b474310bd1efdb
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04879292

Reaction notes

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