N-Fluorobenzenesulfonimide → 3-Fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid

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Reaktionsgleichung

[C:1]1([C:7]2[CH:18]=[CH:17][C:10]3[S:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:34])(=O)=O)=CC=1>C1COCC1>[F:34][C:13]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:18]=[CH:17][C:10]=2[S:11][C:12]=1[C:14]([OH:16])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

To a solution of compound 52c (507 mg, 1.99 mmol) in THF (8 mL) at −70° C. was added n-BuLi (1.6 M in hexane, 2.62 mL, 4.19 mmol). The mixture was stirred at −70° C. for 1 h; then a solution of N-fluorobenzenesulfonimide (817.3 mg, 2.59 mmol) in THF (2 mL) was slowly added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The resulting mixture was partitioned between dilute aqueous HCl and EtOAc. The organic solution was washed with water and brine, dried over Na2SO4, and concentrated. The residue was tritrated from CH2Cl2, filtered and dried the solid to give compound 52d (391.9 mg). MS m/z (M+H+) 273.0.

Aufarbeitung

temperatureto warm to room temperature
stirringwas stirred overnight
customThe resulting mixture was partitioned between dilute aqueous HCl and EtOAc
washThe organic solution was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated
filtrationfiltered
customdried the solid

Quellen und Nachweise

ORD-Eintrag: ord-75071dfaca744072ba005782f23832d7
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08623858B2

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