Bromine → 1-Bromo-2-iodo-4,5-dimethoxybenzene

HRID 1722447

Reaktionsgleichung

Reaktionsgleichung von HRID 1722447
[I:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Br:12]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[Br:12][C:7]1[CH:6]=[C:5]([O:8][CH3:9])[C:4]([O:10][CH3:11])=[CH:3][C:2]=1[I:1]

Komponenten

6

Edukt 3

HCID 24408Bromine2×HCID 2303074-Iodo-1,2-dimethoxybenzeneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 33464041-Bromo-2-iodo-4,5-dimethoxybenzeneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

4-iodoveratrole (26.0 g. 0.0985M) in acetic acid (25 ml) was treated with bromine (6.5 ml. 0.127M) in acetic acid (30 ml) and stirred at room temperature for one hour. The mixture was diluted with water (300 ml) and treated with sodium bisulfite to discharge the excess bromine. The white solid was filtered, washed with water and dried in vacuo over P2O5 to give 4-bromo-5-iodoveratrole (33.0 g, 95% yield) as a white solid, mp 98°-100° C. (literature: Baker et al., J. Chem. Soc. 3986 (1961), mp 102°-104° C.). NMR (CDCl3) δ 3.83 ppm (s, 6H, (2×) OCH3), 7.06 (s, 1H, ArH), 7.21 (s, 1H, ArH).

Aufarbeitung

  1. filtrationThe white solid was filtered
  2. washwashed with water
  3. dry with materialdried in vacuo over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-670c9e6fea614efbbc336d00edef267e
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04855426

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