Triethylamine → 3-Hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne methanesulfonate

HRID 1701820Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Dropwise 13 ml (0.17 mole) of methanesulfonyl chloride was added to a solution of 28.9 g (0.1 mole) of 3-hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne and 24.4 ml (0.175 mole) of triethylamine in 300 ml of methylene chloride which was cooled to 0° C. The mixture was washed with ice water, cold 1 N hydrochloric acid, cold saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. Concentration of the methylene chloride solution gave a brown oil which was crystallized from ether to give a yellow solid. Recrystallization from a mixture of ether and petroleum ether gave off-white prisms, mp 95°-96° C.

Workup

washThe mixture was washed with ice water, cold 1 N hydrochloric acid, cold saturated aqueous sodium bicarbonate
dry with materialdried over anhydrous sodium sulfate
customConcentration of the methylene chloride solution gave a brown oil which
customwas crystallized from ether
customto give a yellow solid
customRecrystallization
additionfrom a mixture of ether and petroleum ether
customgave off-white prisms, mp 95°-96° C.

Sources & evidence

ORD record: ord-6cc49c61e1f949baacffc73718a78926
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04379090

Reaction notes

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