Acetyl chloride → 7-Bromo-1H-2-benzopyran-1,3(4H)-dione

HRID 506967Notes

Reaction equation

HRID 506967 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(O)=[O:2].C(Cl)(=O)C>CC(C)=O>[Br:14][C:11]1[CH:10]=[C:6]2[C:5]([CH2:4][C:1](=[O:2])[O:8][C:7]2=[O:9])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 106349875-Bromo-2-(carboxymethyl)benzoic acid

Product 1

HCID 185077967-Bromo-1H-2-benzopyran-1,3(4H)-dioneYield 99.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-(carboxymethyl)-5-bromobenzoic acid (2.37 g) in acetone (20 ml) was added acetyl chloride (2.60 ml) and the reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated and azeotroped with toluene (×3). The resultant solid was triturated with diethyl ether to yield 7-bromo-1H-isochromene-1,3(4H)-dione as a brown solid (2.20 g); NMR Spectrum: (DMSOd6) 4.24 (s, 2H), 7.42 (d, 1H), 7.94 (d, 1H), 8.13 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. customazeotroped with toluene (×3)
  3. customThe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-b61d3480532f4df98c930fc08176f129
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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