N-bromobutanimide → Methyl 4'-bromomethylbiphenyl-3-carboxylate

HRID 465787

Reaktionsgleichung

Reaktionsgleichung von HRID 465787
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 1394187Methyl 3-(4-methylphenyl)benzoate

Produkt 1

HCID 12019907Methyl 4'-bromomethylbiphenyl-3-carboxylateAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A solution of 7.31 g of Methyl 4'-methylbiphenyl-3-carboxylate, 5.75 g of N-bromosuccinimide, 0.125 g of azo(bisisobutyronitrile), and 500 mL of carbon tetrachloride was refluxed for 3 hours. After cooling to room temperature the resulting suspension was filtered and then concentrated in vacuo to provide 9.90 g of crude methyl 4'-bromomethylbiphenyl-3-carboxylate which was used in a subsequent reaction without further purification; NMR (200 MHz, CDCl3): δ8.28 (s, 1H); 8.05 (d, 1H); 7.79 (d, 1H); 7.67-7.48 (m, 5H); 4.55 (s, 2H); 3.98 (s, 3H).

Aufarbeitung

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fb9f0ef8dd064a8ea1b7c299cb90de20
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153197

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