Chloride → 1-(2-Chloroethyl)-2,4-dinitrobenzene

HRID 1859219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859219
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14]O)([O-:3])=[O:2].C1(C)C=CC=CC=1.N1C=CC=CC=1.[Cl-:29]>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14][Cl:29])([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 1049PyridineHCID 1140Toluene2×HCID 118307342-(2,4-Dinitrophenyl)ethanol

Produkt 1

HCID 123368401-(2-Chloroethyl)-2,4-dinitrobenzeneAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

20 g 2-(2,4-dinitrophenyl)ethanol (94 mmol) are dissolved in 120 ml abs. toluene and 4 ml pyridine. 34 g thidnyl chloride (21 ml, 282 mmol) in 20 ml abs. toluene are quickly added in a drop-wise manner. After 2 h under reflux, this is cooled and poured onto ice. This is mixed with 100 ml CH2Cl2 and the aqueous phase is extracted 2× each with 50 ml CH2Cl2. The combined organic phases are dried over Na2SO4, filtered and rotary evaporated. 21.51 g (93 mmol, 98%) 2-(2,4-dinitrophenyl)ethyl chloride are obtained as a brown oil.

Aufarbeitung

  1. temperatureAfter 2 h under reflux
  2. temperaturethis is cooled
  3. additionpoured onto ice
  4. extractionthe aqueous phase is extracted 2× each with 50 ml CH2Cl2
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-139bf7808fbb4009bfcee226d37629a3
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153744

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