1,3-Dibromopropane → Ethyl-1-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-yl)-cyclo butane carboxylate

HRID 385379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385379
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[H-].[Na+].Br[CH2:33][CH2:34][CH2:35]Br.[NH4+].[Cl-]>CN(C=O)C>[CH2:28]([O:27][C:25]([C:24]1([C:4]2[CH:5]=[C:6]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=3)[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[C:2]([Cl:1])[CH:3]=2)[CH2:35][CH2:34][CH2:33]1)=[O:26])[CH3:29]

Komponenten

6

Edukt 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57995666HCID 57995666, Verbindung

Produkt 1

HCID 57995639Ethyl-1-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-yl)-cyclo butane carboxylateAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)acetate (1.5 g, 3.4 mmol) was dissolved in anhydrous DMF (30 mL), NaH (60% wt. in paraffin oil, 0.163 g, 6.8 mmol) was added at 0° C. The reaction mixture was stirred for 30 min at room temperature and 1,3-dibromopropane (0.757 g, 3.7 mmol) was added drop wise at 0° C. The reaction mixture was stirred for an additional 1 h at 0° C. and saturated NH4Cl solution (10 mL) was added. The reaction mixture was extracted with EtOAc (3×20 mL) and the combined organic phases were washed with water (3×20 mL) and brine (20 mL), and dried over MgSO4. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to yield compound ethyl-1-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-cyclo butane carboxylate (400 mg).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for an additional 1 h at 0° C.
  2. extractionThe reaction mixture was extracted with EtOAc (3×20 mL)
  3. washthe combined organic phases were washed with water (3×20 mL) and brine (20 mL)
  4. dry with materialdried over MgSO4
  5. customThe volatiles were removed under reduced pressure
  6. customthe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-78578a643033440db9f20fbcd657ff2c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367863B2

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