Carbon Dioxide → 7-BROMO-2,3-DIMETHYL-1-BENZOFURAN

HRID 1107863Notes

Reaction equation

HRID 1107863 reaction equation
S(=O)(=O)(O)O.C(=O)=O.[Br:9][C:10]1[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=1[O:12][CH:13]([CH3:17])[C:14](=O)[CH3:15]>CC(C)=O>[CH3:17][C:13]1[O:12][C:11]2[C:10]([Br:9])=[CH:21][CH:20]=[CH:19][C:18]=2[C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 15381110HCID 15381110, compound

Product 1

HCID 110962627-BROMO-2,3-DIMETHYL-1-BENZOFURANYield 91.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25 ml of concentrated sulphuric acid are introduced into a 100 ml three-necked flask equipped with a thermometer and a 10 ml dropping funnel and cooling is carried out to between -15 and 0° C. with a bath of solid carbon dioxide in acetone. 3-(2-Bromophenoxy)-2-butanone (5 g, 20.6 mmol) is added dropwise and stirring is continued for 5 min. The mixture is poured onto crushed ice and then extraction is carried out with ethyl acetate (3×80 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: cyclohexane). 4.24 g (Yield: 91%) of 2,3-dimethyl-7-bromobenzofuran are obtained--M.p.: 33° C.

Workup

  1. customequipped with a thermometer
  2. temperaturecooling
  3. additionThe mixture is poured
  4. customonto crushed ice
  5. extractionextraction
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue is purified by silica column chromatography (elution solvent: cyclohexane)

Sources & evidence

ORD record
ord-3967f8d9b6504b879c696d25a1cd0ce8
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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