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Benzoyl Peroxide → Methyl 5-bromo-2-(bromomethyl)benzoate

HRID 230234
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 230234
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH3:11].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:38]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 316201Methyl 5-bromo-2-methylbenzoate

Produkt 1

HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Bromo-2-methyl-benzoic acid methyl ester (1.31 g, 5.72 mmol) was dissolved in carbon tetrachloride (40 mL). Benzoyl peroxide (10-20 mg) and NBS (1.01 g, 5.72 mmol) were added and the reaction mixture was heated to reflux at 100° C. The reaction course was followed by HPLC and determined to be complete after 1.25 hours. Silica gel was added and the solvent was removed under reduced pressure. The material was purified on silica gel using 5% ethyl acetate in hexanes as the eluent and was determined to be 85% pure by NMR (contained 10% starting material and 5% 5-bromo-2,2-dibromomethyl-benzoic acid methyl ester) and then used without further purification. 1H NMR (300.132 MHz, CDCl3) δ 8.10 (d, J=2.2 Hz, 1H), 7.62 (dd, J=8.3, 2.1 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 4.90 (s, 2H), 4.90 (s, 3H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. additionSilica gel was added
  3. customthe solvent was removed under reduced pressure
  4. customThe material was purified on silica gel using 5% ethyl acetate in hexanes as the eluent
  5. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d587078cc49647c0b401dcc940a3b844
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07566727B2

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