Triethylamine → 2-Methanesulfonyloxy-2-p-tolyl-1,1,1,3,3,3-hexafluoropropane

HRID 861836

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:8][C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([C:4]([F:6])([F:5])[F:7])[C:2]([F:16])([F:17])[F:1])(=[O:28])=[O:27]

Participants

Conditions

Temperature: 5 °C

Procedure

5.16 g (20 mmol) of 1,1,1,3,3,3-hexafluoro-2-p-tolylpropan-2-ol were dissolved in 50 ml of methylene chloride, and 2.8 g (28 mmol) of triethylamine were added. 3.2 g (22 mmol) of methanesulfonyl chloride were added dropwise, while stirring, to the solution cooled to 5° C. After warming up to room temperature, the mixture was allowed to stand overnight. The precipitated salt was filtered off and the organic solution was evaporated down. The subsequent chromatography (silica gel/methylene chloride) gave 4.8 g of 2-methanesulfonyloxy-2-p-tolyl-1,1,1,3,3,3-hexafluoropropane (pale yellow oil).

Workup

temperatureAfter warming up to room temperature
filtrationThe precipitated salt was filtered off
customthe organic solution was evaporated down

Sources & evidence

ORD record: ord-bfa83e74d423487693db90f92360767b
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716756

Linked notes

Loading…