Dichloromethane → HCID 118046905, Verbindung

HRID 63851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63851
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[OH:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].ClCCl.[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([C:27]([F:30])([F:29])[F:28])=[CH2:26])[CH:22]=[C:21]([C:31]([F:34])([F:33])[F:32])[CH:20]=1.[O-]Cl.[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:26][C:25]([C:23]3[CH:22]=[C:21]([C:31]([F:32])([F:33])[F:34])[CH:20]=[C:19]([Cl:18])[CH:24]=3)([C:27]([F:30])([F:29])[F:28])[O:10][N:9]=2)=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 23665760Sodium HypochloriteHCID 86654468HCID 86654468, VerbindungHCID 118046913(NE)-N-[[4-bromo-3-(trifluoromethyl)phenyl]methylidene]hydroxylamine

Produkt 1

HCID 118046905HCID 118046905, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 50-mL round-bottom flask, was placed (E)-N-[[4-bromo-3-(trifluoromethyl)phenyl]methylidene]hydroxylamine (1.5 g, 5.60 mmol, 1.00 equiv), dichloromethane (20 mL), 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.6 g, 5.83 mmol, 1.10 equiv), NaOCl (10 mL). The resulting solution was stirred for 2 h at room temperature. The resulting solution was diluted with 30 mL of H2O. The resulting solution was extracted with 3×50 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3×50 mL of brine. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 1.7 g (56%) of 3-[4-bromo-3-(trifluoromethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a light yellow solid.

Aufarbeitung

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×50 mL of dichloromethane
  3. washThe resulting mixture was washed with 3×50 mL of brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThis resulted in 1.7 g (56%) of 3-[4-bromo-3-(trifluoromethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-a7ba6a442adc43b2bbeb94ef9c884f1a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447084B2

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