N-bromobutanimide → HCID 46830451, Verbindung

HRID 719690

Reaktionsgleichung

Reaktionsgleichung von HRID 719690
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(C2C=CC(C)=CC=2)=CC=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:7]1[C:8]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][Br:19])=[CH:16][CH:17]=2)=[CH:9][CH:10]=[CH:11][CH:6]=1)=[O:24])[CH3:21]

Komponenten

6

Edukt 3

HCID 67184N-bromobutanimideHCID 109226684'-Methyl-biphenyl-2-carboxylic acid ethyl esterHCID 214642554'-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester

Produkt 1

HCID 46830451HCID 46830451, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

4′-Bromomethyl-biphenyl-2-carboxylic acid ethyl ester was prepared in a similar fashion to 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester as described. 4′-Methyl-biphenyl-2-carboxylic acid ethyl ester (5.58 g, 23.22 mmol, 1 eq.) in carbon tetrachloride was treated with N-bromosuccinimide (4.96 g, 27.86 mmol, 1.2 eq.) and 2,2′-azobisisobutyronitrile (0.19 g, 1.16 mmol, 5 mol %). When complete, the reaction was worked up as described to give a yellow oil. The oil was purified by silica gel flash chromatography using 5% EtOAc in hexane as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo to give 4′-bromomethyl-biphenyl-2-carboxylic acid ethyl ester (7.32 g, 99% yield) as a yellow oil.

Aufarbeitung

  1. customto give a yellow oil
  2. customThe oil was purified by silica gel flash chromatography
  3. additionFractions containing the product
  4. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2dad5b957f304916b97aa850493c52ed
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132456B2

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