Allyl bromide → 2-Allyloxy-5-bromobenzoic acid

HRID 427744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427744
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-:12].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C=O)C>[CH2:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[C:7]([OH:12])=[O:8])[CH:18]=[CH2:19]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Produkt 1

HCID 87071652-Allyloxy-5-bromobenzoic acidAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-salicylaldehyde (20.1 g, 100 mM) in DMF (50 ml) was treated with potassium carbonate (20.7 g, 150 mM) and allyl bromide (12.7 g, 10.5 mM). The reaction was stirred at ambient temperature for 18 hours. The reaction was partitioned between ethyl acetate/water. The organic phase was washed with water four times, dried (MgSO4) and evaporated at reduced pressure to give 2-allyloxy-5-bromobenzoic acid as a pale yellow oil (10.0 g, 41 %).

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate/water
  2. washThe organic phase was washed with water four times
  3. dry with materialdried (MgSO4)
  4. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a6fe4789a62481b87e7327836099939
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313148B1

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