Triethylamine → 2-(2-Nitrophenyl)propyl chloroformate

HRID 658513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658513
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:13])[CH2:11][OH:12])([O-:3])=[O:2].C(N(CC)CC)C.O=C(Cl)[O:23][C:24](Cl)(Cl)[Cl:25]>O1CCCC1>[Cl:25][C:24]([O:12][CH2:11][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:13])=[O:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 113897552-(2-Nitrophenyl)propan-1-ol

Produkt 1

HCID 114479052-(2-Nitrophenyl)propyl chloroformateAusbeute 130 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2-(2-nitrophenyl)propanol (16.12 g, 89 mmol) and triethylamine (12.4 mL, 89 mmol) in anhydrous tetrahydrofuran (THF) (96 mL) was added to a cold solution (0° C.) of diphosgene (10.7 mL, 89 mmol) in anhydrous THF (40 mL) over a period of 15 min with stirring and under nitrogen. After 30 min the cooling bath was removed and stirring was continued at room temperature for 3 h. The mixture was filtered and washed with THF. The solvent was removed in vacuo to give 28.20 g of 2-(2-nitrophenyl)propyl chloroformate as light brown oil that was directly used for the next reaction step. TLC: 20% ethyl acetate in hexanes, Rf=0.66.

Aufarbeitung

  1. customAfter 30 min the cooling bath was removed
  2. stirringstirring
  3. filtrationThe mixture was filtered
  4. washwashed with THF
  5. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-58943d3abc68468ab4521f82bd5246e6
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076501B2

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