N-bromobutanimide → 5-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene

HRID 1880431

Reaktionsgleichung

Reaktionsgleichung von HRID 1880431
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[C:4]([CH2:10][Br:11])[CH:3]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 27362985-Bromo-2-fluoro-1,3-dimethylbenzene

Produkt 1

HCID 669206545-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzeneAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromo-2-fluoro-1,3-dimethylbenzene (5.0 g, 25 mmol) in carbon tetrachloride (100.0 mL) was added N-bromosuccinimide (4.11 g, 23.1 mmol) and benzoyl peroxide (100.0 mg, 0.017 mmol). The reaction was heated at reflux for 7 hours. The reaction was filtered and the filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was flash chromatographed (5% EtoAc/Haptanes) to obtain 6.56 g of 5-bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene as an oil product. 1H NMR (400 MHz, CDCl3) δ ppm 2.22-2.36 (s, 3 H) 4.42 (d, J=0.98 Hz, 2 H) 7.21-7.37 (m, 2 H)

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 7 hours
  3. filtrationThe reaction was filtered
  4. washthe filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (5% EtoAc/Haptanes)

Quellen und Nachweise

ORD-Eintrag
ord-4b345bc30f60488db40c42acdba3cf03
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318762B2

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