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

HRID 1155949

Reaction equation

HRID 1155949 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-08b44c19d50a487ba35eaa88d01d0b12
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Linked notes

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