Iodine → HCID 59234900, compound

HRID 1919757Notes

Reaction equation

[I:1]I.[F:3][C:4]([F:25])([F:24])[C:5]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH2:21][CH2:22][CH3:23])[CH:15]=1)([O:10][CH2:11][O:12][CH3:13])[C:6]([F:9])([F:8])[F:7].S([O-])([O-])(=O)=S.[Na+].[Na+]>N1C=CC=CC=1>[F:3][C:4]([F:24])([F:25])[C:5]([C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][CH3:23])[C:17]([OH:20])=[C:18]([I:1])[CH:19]=1)([O:10][CH2:11][O:12][CH3:13])[C:6]([F:8])([F:7])[F:9]

Participants

Conditions

Temperature: 60 °C

Procedure

Iodine (13.3 g) was added to a mixed solution of 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenol (3.63 g, 10.5 mmol) in pyridine (50 mL) at room temperature, followed by heating in an oil bath at an external temperature of 60° C. overnight. A 1 mol/L sodium thiosulfate aqueous solution was added to the reaction solution at room temperature, followed by extraction with ethyl acetate-water. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 4.20 g of the title compound (yield: 85%) as a brown solid.

Workup

extractionfollowed by extraction with ethyl acetate-water
concentrationThe organic layer was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-a04e4a77839142dc9778514a0336e888
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168666B2

Reaction notes

Loading…