Thionyl bromide → HCID 18761815, Verbindung

HRID 432046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432046
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(Br)([Br:21])=O>C1(C)C=CC=CC=1>[Br:21][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2

Komponenten

4

Edukt 2

HCID 68176Thionyl bromideHCID 99211661-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol

Produkt 1

HCID 18761815HCID 18761815, VerbindungAusbeute 103,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 5-hydroxymethyl-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (2 g, 8.2 mmol) in toluene (20 mL) was heated until the solid dissolved. Heating was then stopped. Thionyl bromide (2.2 g, 10.6 mmol) was added, and the mixture was stirred for 1 h. Silica (25 g) was added, and the mixture was filtered, and the residue was washed with a 1:1 v/v solution of ethyl acetate and heptane. The filtrate was evaporated to give the title compound as a red-orange oil (2.6 g, 90%). 1H NMR (d6-DMSO): δ 4.72 (s, 2H), 5.11 (d, 1H), 5.28 (d, 1H), 6.17 (s, 1H), 7.04 (d, 1H), 7.17 (t, 2H), 7.33 (d, 1H), 7.38 (dd, 2H), 7.45 (s, 1H).

Aufarbeitung

  1. temperaturewas heated until the solid
  2. dissolutiondissolved
  3. temperatureHeating
  4. additionSilica (25 g) was added
  5. filtrationthe mixture was filtered
  6. washthe residue was washed with a 1:1 v/v solution of ethyl acetate and heptane
  7. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a24a41cb4b4b43679ed8ced00790292f
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660873B2

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