Phosphorus tribromide → 5-(Benzyloxy)-2-(bromomethyl)-1,3-dimethylbenzene

HRID 1013807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013807
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16]O)=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:20]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][Br:20])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 67317571(4-(Benzyloxy)-2,6-dimethylphenyl)methanol

Produkt 1

HCID 114267005-(Benzyloxy)-2-(bromomethyl)-1,3-dimethylbenzeneAusbeute 247,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cool a solution of (4-Benzyloxy-2,6-dimethyl-phenyl)-methanol (5.70 g, 24 mmol) in THF (100 mL) to 0° C. Treat the solution with Phosphorous tribromide (0.9 mL, 9.4 mmol) and stir the reaction for 2 hr at 0° C. Quench the reaction with water and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 7.1 g (99%) of product. 1H NMR (d6-CDCl3) δ 7.31-7.43 (m, 5H), 6.65 (s, 2H), 5.01 (s, 2H), 4.56 (s, 2H), 2.38 (s, 6H).

Aufarbeitung

  1. customthe reaction for 2 hr at 0° C
  2. customQuench
  3. customthe reaction with water
  4. extractionextract with Et2O
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-65e8a7db406c4bd993831213a1943845
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981918B2

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