Sodium Bicarbonate → 4-Bromo-2-benzofuran-1[3H]-one

HRID 2171012Notes

Reaction equation

HRID 2171012 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[CH3:11].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]2[C:5]=1[CH2:11][O:2][C:3]2=[O:12]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 115937154-Bromo-2-benzofuran-1[3H]-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of 3-Bromo-2-methyl-benzoic acid methyl ester (500 mg, 2.22 mmol) in carbon tetrachloride (6 mL) at 0° C., was added chromylchloride (0.36 mL, 4.45 mmol) and the reaction mixture was heated to reflux for 20 h. The reaction mixture was cooled to RT, added ice water and sat sodium bicarbonate solution at 0° C. Extracted with ethyl acetate (3×) the combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-10% ethyl acetate in pet. ether) afforded 4-bromo-3H-isobenzofuran-1-one as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 20 h
  3. customat 0° C
  4. extractionExtracted with ethyl acetate (3×) the combined ethyl acetate layer
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (silica gel, 0-10% ethyl acetate in pet. ether)

Sources & evidence

ORD record
ord-c2382dccc6464bd7b33bba5b1b0bb1de
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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