Sulfuric Acid → 1-Fluoro-4-(4-iodophenoxy)benzene

HRID 526759

Reaktionsgleichung

[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10](N)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:25].[Na+]>COCCOC.O>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([I:25])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

To a stirred solution of 4-(4-fluorophenoxy)benzenamine (3.4 g, 16.73 mmol, 1.00 equiv) in ethylene glycol dimethyl ether (45 mL) was added dropwise a solution of 50% sulfuric acid (7 mL) in water (34 mL) at room temperature. The reaction was cooled to −5° C. and a solution of sodium nitrite (1.73 g, 25.07 mmol, 1.50 equiv) in water (12 mL) was then added dropwise within 30 min. The resulting solution was stirred for 30 min at −5-0° C. then a solution of sodium iodide (12.6 g, 84.00 mmol, 5.02 equiv) in water (34 mL) was added dropwise at −5-0° C. After stirring for 30 min at −5-0° C., the solution was extracted with 3×200 mL of ethyl acetate. The combined organic layers was washed with 3×200 mL of saturated Na2SO3 solution, dried over anhydrous sodium sulfate and concentrated under vacuum to give 5.0 g (95%) of 1-fluoro-4-(4-iodophenoxy)benzene as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 7.62-7.57 (m, 2H), 7.08-6.93 (m, 4H), 6.77-6.70 (m, 2H) ppm.

Aufarbeitung

stirringAfter stirring for 30 min at −5-0° C.
extractionthe solution was extracted with 3×200 mL of ethyl acetate
washThe combined organic layers was washed with 3×200 mL of saturated Na2SO3 solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-b0331d27cbbc47909138a1f2d2164b0b
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09346761B2

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