Iodine → 5-Bromo-3,3-dimethylbenzofuran-2(3H)-one

HRID 444075

Reaktionsgleichung

Reaktionsgleichung von HRID 444075
[CH3:1][C:2]1([CH3:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:11].II.[Br:15]Br>C(Cl)(Cl)(Cl)Cl.[Fe]>[Br:15][C:8]1[CH:9]=[CH:10][C:5]2[O:4][C:3](=[O:11])[C:2]([CH3:12])([CH3:1])[C:6]=2[CH:7]=1

Komponenten

6

Edukt 3

HCID 807IodineHCID 24408BromineHCID 5956202(3H)-Benzofuranone, 3,3-dimethyl-

Produkt 1

HCID 162206345-Bromo-3,3-dimethylbenzofuran-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

2,3-Dihydro-3,3-dimethylbenzofuran-2-one (1.62 g, 0.01 mole), in carbon tetrachloride (25 ml) containing catalytic amounts of iron filings and iodine was treated with bromine (1.6 g, 0.01 mole) and the mixture boiled under reflux for 1 hour. The solvent was removed under vacuum and the residue taken up in petroleum ether (b.p. 60°-80° C.). The solution was decanted from a little insoluble residue and washed with aqueous sodium metabisulphite and water, dried over magnesium sulphate and run down. The title product was obtained as a white solid m.p. 49°-53° C. and was shown by NMR to be a slightly impure sample of the product obtained in Example 3(b).

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. customThe solvent was removed under vacuum
  3. customThe solution was decanted from a little insoluble residue
  4. washwashed with aqueous sodium metabisulphite and water
  5. dry with materialdried over magnesium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-e80750713554475f8b42d2bf142d562b
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263037

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