Benzene, 1-fluoro-4-[(4-nitrophenyl)sulfonyl]- → 4-((4-Fluorophenyl)sulfonyl)aniline

HRID 1795784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795784
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Rh]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Komponenten

4

Edukt 1

HCID 22179363Benzene, 1-fluoro-4-[(4-nitrophenyl)sulfonyl]-

Produkt 1

HCID 5728144-((4-Fluorophenyl)sulfonyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-fluorophenyl 4-nitrophenyl sulfone (1.89 g, 6.72 mmol) in methanol (80 mL) is treated with Rhodium on carbon (5%, 95 mg) and hydrogenated at 20 psi for 24 hr. The mixture is filtered, rinsing with methylene chloride (2×100 mL) and methanol (100 mL). The filtrate is concentrated to near dryness and refiltered, rinsing with minimal methanol. The solid is dried in the vacuum oven at 500 to give the desired amine, mp=204–205°: IR (drift) 3473, 3373, 1638, 1592, 1489, 1303, 1294, 1285, 1231, 1159, 1144, 1107, 834, 713 and 689 cm−1; NMR (300 MHz, CDCl3) 7.80–7.95, 7.60–7.75, 7.13, 6.60–6.75 and 4.17 δ; MS (EI) m/z 251 (M+), 140, 108, 95, 92, 80, 65, 65, 63 and 51.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. washrinsing with methylene chloride (2×100 mL) and methanol (100 mL)
  3. concentrationThe filtrate is concentrated
  4. washrinsing with minimal methanol
  5. customThe solid is dried in the vacuum oven at 500

Quellen und Nachweise

ORD-Eintrag
ord-913f6153aad24f5c9468b43c8927d2bf
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030109B2

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