Trichlorofluoromethane → 5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid

HRID 437318

Reaction equation

[CH3:1][C:2]1[C:3](=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:24])=[O:23])=[CH:18][CH:17]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.[F:25]C(Cl)(Cl)Cl.FOC(F)(F)F>>[F:25][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:24])=[O:23])=[CH:18][CH:17]=1)[C:2]([CH3:1])=[C:10]2[CH2:11][C:12]([OH:14])=[O:13]

Participants

Reactant 3

HCID 6389Trichlorofluoromethane

HCID 78989Hypofluorous acid, trifluoromethyl ester

HCID 54462256HCID 54462256, compound

Product 1

HCID 53525-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid

Conditions

Temperature: -15 °C

Procedure

2-Methyl-1-(p-methylsulfinylbenzylidene)inden-3-acetic acid (2.25 g.) dissolved in 80 ml. of fluorotrichloromethane was ultraviolet irradiated and stirred at -15° C. for 80 min.; meanwhile 1.2 g. of fluoroxytrifluoromethane was passed in. The residue obtained after evaporation of the solvent was subjected to chromatography on a silica gel column, to give 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)inden-3-acetic acid, m.p. 188°-189° C.

Workup

customThe residue obtained
customafter evaporation of the solvent

Sources & evidence

ORD record: ord-66baa80bd4b84666895fb2918415098e
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04030994

Linked notes

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