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

HRID 2417568Notes

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 1N 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 1N 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-2d046880ae2f4596a2bed50c53e8b9d5
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04469633

Reaction notes

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