o-Toluenesulfonyl chloride → HCID 88196538, compound

HRID 374735Notes

Reaction equation

HRID 374735 reaction equation
[F:1][C:2]([F:30])([O:9][C:10]([F:29])([F:28])[C:11]([F:27])([F:26])[O:12][C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]O.[C:31]1([CH3:41])[C:32]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=1.C(N(CC)C(C)C)(C)C>ClCCl>[C:31]1([CH3:41])[C:32]([S:37]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:30])[O:9][C:10]([F:28])([F:29])[C:11]([F:26])([F:27])[O:12][C:13]([F:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:17])([F:18])[F:19])(=[O:39])=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 8623o-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54296596HCID 54296596, compound

Product 1

HCID 88196538HCID 88196538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This hexanol (1.2 g, 2.45 Moles)was combined with toluene sulfonyl chloride (0.5 g, 2.58 mmoles), N,N-diisopropylethyl amine (0.85 mL, 4.9 mmoles), and N,N-dimethylaminopyridine (12 mg, 0.98 mmole) in dichloromethane (10 mL). After stirring for 10 hours at room temperature, the desired product, 1-toluenesulfonyl-6,6-difluoro-6-(perfluoro-2-butoxyethoxy)hexane, was isolated by column chromatography (and its structure confirmed by infrared spectroscopy).

Sources & evidence

ORD record
ord-6a32166e239548fd991804aab3bc2bc3
Source dataset
uspto-grants-1996_01
Patent number
US05482650

Reaction notes

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