1-Chloro-4-fluoro-2-nitrobenzene → 2-Amino-4-fluorobenzene-1-thiol

HRID 57223

Reaktionsgleichung

Reaktionsgleichung von HRID 57223
Cl[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-])=O.O.O.O.O.O.O.O.O.O.[S-2:21].[Na+].[Na+]>O>[NH2:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[SH:21]

Komponenten

4

Edukt 2

HCID 676591-Chloro-4-fluoro-2-nitrobenzeneHCID 73972Sodium sulfide nonahydrate

Produkt 1

HCID 111054802-Amino-4-fluorobenzene-1-thiolAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-5-fluoronitrobenzene (1.81 g, 10.31 mmol) dissolved in 30 mL of deionized water at room temperature was added sodium sulfide nonahydrate (9.90 g, 41.24 mmol) in a single portion. The resulting solution was heated to reflux and stirred under nitrogen for 32 hours. The resulting light yellow solution was then cooled to room temperature and was washed with 5×50 mL of ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to yield a yellow oil. The crude material was purified by flash chromatography eluting with CH2Cl2:MeOH=10:1 to yield 0.36 g (25%) of the title compound. MS (m/z, ES+): 144.0 (M+1, 100%); IR (KBr): 3430, 3340, 1615, 1573, 1482, 1281, 1248, 1172, 1124, 1044, 975, 840, 792 cm−1; 1H NMR (300 MHz, ppm, DMSO-d6) δ: 6.89 (dt, 1H), 6.50 (dd, 1H), 6.21 (dt, 1H), 5.80 (br s, 2H).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. washwas washed with 5×50 mL of ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a yellow oil
  8. customThe crude material was purified by flash chromatography
  9. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-d98aab770b55417f9a9a18e5bcdce437
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434720B2

Verknüpfte Notizen

Wird geladen…