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Water → 2-(Benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acid

HRID 505653
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505653
[CH2:1]([O:8][CH2:9][C:10]1[CH:18]=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:27]N1C(=O)CCC1=O.O>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]1[C:18]([Br:27])=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 687174092-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid

Produkt 1

HCID 866163832-(Benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acidAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid (60 mg, 0.17 mmol) obtained in Step 6 of Example 22 was dissolved in N,N-dimethylformamide (10 mL), and N-bromosuccinimide (62 mg, 0.35 mmol) was added thereto followed by stirring at a room temperature for 2 hours. The reaction mixture was added with water and extracted with chloroform 3 times. The organic layers were combined and sequentially washed with saturated aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain 2-(benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acid (16 mg, 22%).

Aufarbeitung

  1. extractionextracted with chloroform 3 times
  2. washsequentially washed with saturated aqueous sodium thiosulfate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-2d5e4cc771df4346a6df611b0ac701ec
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781485B2

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