Imidazole → 1-(Bromomethyl)-3-ethylbenzene

HRID 2045839

Reaktionsgleichung

Reaktionsgleichung von HRID 2045839
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[CH2:27]([C:29]1[CH:30]=[C:31]([CH2:35]O)[CH:32]=[CH:33][CH:34]=1)[CH3:28]>C(Cl)Cl>[Br:1][CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH2:27][CH3:28])[CH:30]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 104659(3-Ethylphenyl)methanol

Produkt 1

HCID 220036561-(Bromomethyl)-3-ethylbenzeneAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Bromine (0.21 mL, 4.08 mmol) was added dropwise to a solution of triphenylphosphine (1.08 g, 4.12 mmol) and imidazole (280 mg, 4.11 mmol) in CH2Cl2 (13.5 mL) at 0° C. The mixture was allowed to warm to room temperature and then a solution of (3-ethylphenyl)methanol (˜3.05 mmol) in CH2Cl2 (3.5 mL) was added. After 1 h, the mixture was diluted with hexanes and filtered through celite, washing with excess hexanes. The filtrate was concentrated in vacuo. Purification of the crude residue by chromatography on silica gel (hexanes→10% EtOAc/hexanes, gradient) afforded 530 mg (87% over two steps) of 1-(bromomethyl)-3-ethylbenzene.

Aufarbeitung

  1. filtrationfiltered through celite
  2. washwashing with excess hexanes
  3. concentrationThe filtrate was concentrated in vacuo
  4. customPurification of the crude residue by chromatography on silica gel (hexanes→10% EtOAc/hexanes, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-52d018b5833d4dabba78049eae925ad8
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592413B2

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