4-Toluenesulfonyl chloride → 3-Fluoroprop-1-yl toluene-4-sulphonate

HRID 2262599Notes

Reaction equation

HRID 2262599 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>ClCCl>[F:1][CH2:2][CH2:3][CH2:4][O:5][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 680423-Fluoro-1-propanol

Product 1

HCID 63667743-Fluoroprop-1-yl toluene-4-sulphonateYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of 3-fluoro-propanol (64.03 mmol) and 18 ml of triethylamine (129.32 mmol) were dissolved in 50 ml of dichloromethane. At 0-5° C., 12.9 g toluene-4-sulfonylchloride (67.66 mmol) were added and the reaction mixture stirred at room temperature for 18 h. Standard work-up yielded 13.7 g of toluene-4-sulfonic acid 3-fluoro-propyl ester.

Sources & evidence

ORD record
ord-9d70f25c1a044a41881f6cc6b9e40004
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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