Benzene, 1-bromo-3-(trifluoromethyl)- → 2,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-ol

HRID 262138

Reaktionsgleichung

Reaktionsgleichung von HRID 262138
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:13][C:14]1([CH3:26])[CH2:23][C:22](=O)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1.[Cl-].[NH4+]>CCOCC>[CH3:13][C:14]1([CH3:26])[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1

Komponenten

6

Edukt 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

Produkt 1

HCID 120717572,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-olAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

3-Bromobenzotrifluoride (61 g) in dry ether (100 ml) was added to magnesium (6.6 g) in ether (50 ml). 2,2-Dimethylchroman-4-one-7-ol (17.4 g) suspended in ether (500 ml) was added and the mixture refluxed for 16 hourss. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The combined ether layers were washed with 2 N HCl (2×100 ml) and dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound (25 g), m.p. 102°-106° C.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture refluxed for 16 hourss
  3. extractionextracted with ether
  4. washThe combined ether layers were washed with 2 N HCl (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-38c1fdbfa4fd41cebf2cc7138c084fcc
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153617

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