Triethylamine → 2-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dione

HRID 8953

Reaktionsgleichung

Reaktionsgleichung von HRID 8953
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].CCN(CC)CC.[Br:20][CH2:21][C:22]1[C:23]([CH2:28]Br)=[CH:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[Br:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 66665o-Bis(bromomethyl)benzene

Produkt 1

HCID 219851622-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dioneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of N-hydroxyphthalimide (0.60 g, 3.68 mmol) and Et3N (0.60 mL, 4.30 mmol) in DMF (6 mL) was added α,α′-dibromo-o-xylene (3.30 g, 0.0125 mol) and the mixture stirred at room temperature for 4 h. The resultant brown precipitate was filtered and washed with CH2Cl2. The filtrate was diluted with EtOAc (40 mL) and water (30 mL) and the organic phase washed with brine (1×30 mL), dried (Na2SO4) and concentrated under reduced pressure. The resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc) to give the title compound (581 mg, 46%) as a white solid. 1H NMR (CDCl3) δ 4.99 (s, 2H), 5.37 (s, 2H), 7.27–7.40 (m, 2H), 7.41–7.45 (m, 2H), 7.73–7.76 (m, 2H), 7.81–7.84 (m, 2H).

Aufarbeitung

  1. filtrationThe resultant brown precipitate was filtered
  2. washwashed with CH2Cl2
  3. additionThe filtrate was diluted with EtOAc (40 mL) and water (30 mL)
  4. washthe organic phase washed with brine (1×30 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-08381d0f80044bf994b13f6803c6eb40
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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