Benzyl Bromide → 2-(Benzyloxy)-4-bromo-1-methoxybenzene

HRID 1685641

Reaktionsgleichung

Reaktionsgleichung von HRID 1685641
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([OH:10])[CH:9]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:10][C:8]1[CH:9]=[C:4]([Br:3])[CH:5]=[CH:6][C:7]=1[O:11][CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1422285-Bromo-2-methoxyphenol

Produkt 1

HCID 149128522-(Benzyloxy)-4-bromo-1-methoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH, 60% dispersion in mineral oil (0.61 g, 15.3 mmol) was added in three equal portions to DMF (25 mL) pre-cooled to 0° C. 5-Bromo-2-methoxyphenol (2.60 g, 12.8 mmol) was then added in three portions, and the resulting brown solution was stirred for 20 min. Benzyl bromide (2.63 g, 15.3 mmol) was added and the reaction mixture was allowed to warm to room temperature and was stirred overnight resulting in the formation of a yellow solution. The reaction mixture was poured onto H2O (40 mL) leading to the formation of a white precipitate which was extracted into EtOAc (4×50 mL). The combined organics were washed with H2O (4×75 mL), brine (75 mL), dried (MgSO4) and the solvent was removed in vacuo. The crude product was obtained as a white solid which was purified by recrystallisation from Et2O to give the title compound (2.90 g, 77%, mp 109-110° C. [lit. 105-106° C. (Et2O)]Aust. J. Chem., 1981, 34 587) as a white crystalline solid; δH (270 MHz, CDCl3) 7.47-7.26 (5H, m, ArH), 7.07-7.00 (2H, m, ArH), 6.74 (1H, d, J=8.7, ArH), 5.10 (2H, s, CH2), 3.85 (3H, s, CH3), LRMS (FAB+) 294.0 ([M+H]+, 35%), 292.0 (35), 91.1 (100).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringwas stirred overnight
  3. customresulting in the formation of a yellow solution
  4. additionThe reaction mixture was poured onto H2O (40 mL)
  5. extractionwas extracted into EtOAc (4×50 mL)
  6. washThe combined organics were washed with H2O (4×75 mL), brine (75 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo
  9. customThe crude product was obtained as a white solid which
  10. customwas purified by recrystallisation from Et2O

Quellen und Nachweise

ORD-Eintrag
ord-1ea704d94f374d679d5ec2bf0454bb05
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

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