Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

HRID 415172

Reaktionsgleichung

Reaktionsgleichung von HRID 415172
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 7455Methyl 4-methylbenzoateHCID 67184N-bromobutanimide

Produkt 1

HCID 256687Methyl 4-(bromomethyl)benzoateAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Methyl 4-methylbenzoate 3 (2.9 g, 19.3 mmol) was dissolved in tetrachloromethane (CCl4, 20 mL) at room temperature. N-bromosuccinimide (NBS, 3.5 g, 19.0 mmol) and benzoyl peroxide (BPO, 0.26 g, 1.9 mmol) was added. The resulting mixture was stirred at reflux for 5 hr, then cooled to room temperature, washed with saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1) to get a white solid of methyl 4-(bromomethyl)benzoate (4.3 g, 97%), LC-MS (ESI) m/z 230 [M+1]+.

Aufarbeitung

  1. temperatureat reflux for 5 hr
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried with anhydrous sodium sulfate and condensed under vacuum
  4. customThe residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a473a965e5e4d0b97aca180d7b8ba63
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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