Benzoyl Peroxide → Biphenyl-4-yl-bromo-acetic acid methyl ester

HRID 539848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539848
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC#N.O>C(Cl)(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[Br:18]

Komponenten

7

Edukt 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 30808634-Biphenylylacetic acid methyl esterHCID 18373917Acetonitrile--water (1/1)

Produkt 1

HCID 11822880Biphenyl-4-yl-bromo-acetic acid methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of biphenyl-4-yl-acetic acid methyl ester (5 g., 22.1 mmol) in carbon tetrachloride (from Acros, 16772) (25 mL) was added N-bromosuccinimide (from Aldrich, 18350) (3.9 g., 22.1 mmol) and benzoyl peroxide (from Acros, 21178) (0.54 g, 2.2 mmol) and the reaction was heated to reflux for 48 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated in vacuo to afford Cpd. 2 as a crude yellow oil (6.24 g., 93% yield). 1HNMR (CDCl3) δH, 3.81, 3H (s, CH3), 5.41, 1H (s, Br—CH), 7.33-7.39, 2H (m, Ar—H), 7.41-7.46, 3H (m, Ar—H), 7.54-7.63, 4H (m, Ar—H); LCMS analysis (solvent MeCN/H2O/0.1% HCO2H, 5-95% gradient/H2O 2.5 min, 95% 4 min., Phenomenex C18 reverse phase, flow rate 1 mL/min.) HPLC retention time 4.39 min.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto afford Cpd

Quellen und Nachweise

ORD-Eintrag
ord-2b653551695c4e319803072aed7ec319
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871772B2

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