Bromochloromethane → Chloromethyl 3-Benzyloxybenzoate

HRID 1167600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167600
[K].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:20][Cl:21]>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O:15][CH2:20][Cl:21])=[O:14])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 6333BromochloromethaneHCID 3092263-(Benzyloxy)benzoic acidHCID 5462222Potassium

Produkt 1

HCID 22993327Chloromethyl 3-Benzyloxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the potassium salt of 3-benzyloxybenzoic acid (2.39 g, 8.91 mmol) was added the bromochloromethane (8.7 ml, 15 eq.) and DMF (10.7 mL). The mixture was then stirred at room temperature for 12-18 hours. The mixture was then filtered and the filtrate concentrated. Purification of the crude product via flash chromatography (EtOAc:Hexanes 1:10) yielded 1.2 g of the title compound as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ=5.12 (s, 2H), 5.96 (s, 2H), 7.22-7.25 (m, 1H), 7.26-7.47 (m, 6H), 7.68-7.72 (m, 2H), MS(ESI) 276.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated
  3. customPurification of the crude product via flash chromatography (EtOAc:Hexanes 1:10)

Quellen und Nachweise

ORD-Eintrag
ord-8ba2acfed9884aea9b023aacc90ab62a
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620799B2

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