Hydrochloric Acid → 3-Bromo-4-fluorobenzene-1-sulfonyl chloride

HRID 723273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723273
[ClH:1].[Br:2][C:3]1[CH:4]=[C:5](N)[CH:6]=[CH:7][C:8]=1[F:9].C(O[N+]([O-])=O)(C)(C)C.[S:19](=[O:21])=[O:20]>C(Cl)Cl.CO.[Cu](Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([S:19]([Cl:1])(=[O:21])=[O:20])[CH:6]=[CH:7][C:8]=1[F:9]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 27792863-Bromo-4-fluoroaniline

Produkt 1

HCID 218867333-Bromo-4-fluorobenzene-1-sulfonyl chlorideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 21226129Dichloromethane methanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Concentrated HCl (1.93 mL, 23.16 mmol) was added to a solution of 3-bromo-4-fluoro-phenylamine ((Example 265: part a) 2.2 g, 11.58 mmol) in 18 mL of 2:1 DCM/MeOH. A precipitate appeared and another 9 mL of 2:1 DCM/MeOH was added. The solution was cooled to −5° C. and tert-butylnitrate (2.71 mL, 23.16 mmol) was added dropwise over 8 min. After stirring for 15 min, sulfur dioxide (˜5 mL) was condensed into the reaction, followed by addition of copper(II) chloride (592 mg, 3.47 mmol) (gas evolution). The solvent was removed in vacuo and the residue was purified by SiO2 flash column chromatography to yield the title compound (1.9 g, 59%). 1H-NMR (CDCl3): δ 8.31 (dd, 1H, J=2.3, 5.8 Hz), 8.04 (ddd, 1H, J=2.6, 4.1, 8.8 Hz), 7.39 (dd, 1H, J=7.7, 8.8 Hz).

Aufarbeitung

  1. customcondensed
  2. custominto the reaction
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by SiO2 flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ed47e502d7424e55a26c8bd68105e74d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138530B2

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