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Phosgene → 3-[2-Fluoro-5-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride

HRID 2371727
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371727
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C(C2C=CC=CC=2)[N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=3[F:33])[CH2:19]2)C=CC=CC=1>C(Cl)Cl>[F:33][C:24]1[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:32])[F:31])=[CH:28][C:23]=1[O:22][CH:20]1[CH2:19][N:18]([C:1]([Cl:4])=[O:2])[CH2:21]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 199062271-(Diphenylmethyl)-3-[2-fluoro-5-(trifluoromethyl)phenoxy]azetidine

Produkt 1

HCID 150422333-[2-Fluoro-5-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chlorideAusbeute 163,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A mixture of 10.8 g (0.11 mole) of phosgene and 14.2 g (0.11 mole) of potassium carbonate in 200 mL of methylene chloride was cooled to 5° C. in an ice bath while stirring undr nitrogen. After 30 min, the reaction mixture was treated with 40 g (0.1 mole) of 1-(diphenylmethyl)-3-[2-fluoro-5-(trifluoromethyl)phenoxy]azetidine in 100 mL of methylene chloride added dropwise. After stirring for 16 h, the reaction mixture was treated with small pieces of ice to destroy any excess phosgene. Then the reaction mixture was decanted from the inorganic paste and concentrated in vacuo to give 48.6 g of pale yellow oil. The residual oil was distilled at 0.15 mmHg to yield 3 fractions: #1, 12.7 g at 120°-128°; #2, 1.5 g at 128°, and #3 at 128°-132°; with total yield of 19.7 g (66.2%). A sample of fraction #2 was submitted for analysis.

Aufarbeitung

  1. additionadded dropwise
  2. stirringAfter stirring for 16 h
  3. additionthe reaction mixture was treated with small pieces of ice
  4. customto destroy any excess phosgene
  5. customThen the reaction mixture was decanted from the inorganic paste
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1f2211643d4d4312b70bea3b5be5d3b9
Quelldatensatz
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05095014

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