N-bromobutanimide → 4'-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester

HRID 719682

Reaktionsgleichung

Reaktionsgleichung von HRID 719682
C(OC([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][Br:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)=O)C.[CH2:20]([O:22][C:23](C1C=CC(C2C=CC(C)=CC=2)=CC=1)=[O:24])[CH3:21].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:20]([O:22][C:23]([C:11]1[CH:6]=[CH:7][C:8]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][Br:19])=[CH:16][CH:17]=2)=[CH:9][CH:10]=1)=[O:24])[CH3:21]

Komponenten

6

Edukt 3

HCID 67184N-bromobutanimideHCID 118315464'-Methyl-biphenyl-4-carboxylic acid ethyl esterHCID 214642554'-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester

Produkt 1

HCID 135861014'-Bromomethyl-biphenyl-4-carboxylic acid ethyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

4′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester was prepared as described for 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester. 4′-Methyl-biphenyl-4-carboxylic acid ethyl ester (3.4 g, 14.15 mmol, 1 eq.) was reacted with N-bromosuccinimide (3.27 g, 18.4 mmol, 1.3 eq.) and 2,2′-azobisisobutyronitrile (0.12 g, 0.71 mmol, 5 mol %) in carbon tetrachloride (150 mL). When complete, the reaction was worked up as described to produce 4′-bromomethyl-biphenyl-4-carboxylic acid ethyl ester (3.74 g, 83% yield) as a yellow solid.

Aufarbeitung

  1. custom4′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester was prepared

Quellen und Nachweise

ORD-Eintrag
ord-258d8683ab824f1c8d8d37b67c36f9d0
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132456B2

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