Toluene → HCID 15406176, compound

HRID 992168Notes

Reaction equation

[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[CH2:10]([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])[CH2:11][OH:12].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[K+]>[C:1]([O:5][C:6](=[O:9])[CH2:7][O:12][CH2:11][CH2:10][C:13]([F:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:17])([F:19])[F:18])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

29.54 g (151.5 mmol) of bromoacetic acid-tert-butyl ester is added in drops to a mixture of 20 g (75.73 mmol) of 1H,1H,2H,2H-perfluorohexan-1-ol and 2.57 g (7.57 mmol) of tetrabutylammonium hydrogen sulfate in 300 ml of 60% aqueous potassium hydroxide solution/200 ml of toluene while being stirred vigorously at 0° C. It is stirred for 1 hour at 0° C. 100 ml of toluene is added, the aqueous phase is separated and extracted twice with 50 ml of toluene. The combined organic phases are dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel (mobile solvent: hexane/dichloromethane/acetone=20/10/1).

Workup

stirringIt is stirred for 1 hour at 0° C
customthe aqueous phase is separated
extractionextracted twice with 50 ml of toluene
customThe combined organic phases are dried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum
customThe residue is chromatographed on silica gel (mobile solvent: hexane/dichloromethane/acetone=20/10/1)

Sources & evidence

ORD record: ord-13b86eb837ae44fa93637d83002553b6
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468502B1

Reaction notes

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