Carbon tetrabromide → Ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoate

HRID 2121850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121850
O[CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[Br:39][CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15229879Ethyl 2-[4-(2-hydroxy-ethyl)-phenoxy]-2-methyl-propionate

Produkt 1

HCID 15229877Ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoateAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 2-[4-(2-hydroxyethyl)phenoxy]-2-methylpropionate (474 mg) and triphenylphosphine (591 mg) in dichloromethane (10 ml) was added carbon tetrabromide (748 mg) under ice-cooling, and the mixture was stirred for 40 minutes. Rough purification of the reaction mixture by flash column chromatography on silica gel (eluent:diethyl ether) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent:hexane/diethyl ether=10/1) gave ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropionate (500 mg).

Aufarbeitung

  1. temperaturecooling
  2. customRough purification of the reaction mixture by flash column chromatography
  3. customon silica gel (eluent:diethyl ether) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent:hexane/diethyl ether=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-bc453cdf38314272bb5aeda161572db9
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696489B1

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