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

HRID 444075

Reaction equation

HRID 444075 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e80750713554475f8b42d2bf142d562b
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Linked notes

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