Acetyl chloride → 6-Bromoisochroman-1,3-dione

HRID 927267Notes

Reaction equation

HRID 927267 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:3]=1.C(Cl)(=O)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:8])[O:14][C:12](=[O:13])[CH2:11]2

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 534401324-Bromo-2-(carboxymethyl)benzoic acid

Product 1

HCID 217824866-Bromoisochroman-1,3-dioneYield 79.5%

Conditions

Temperature
150 °C

Procedure

A mixture of 4-bromo-2-(carboxymethyl)benzoic acid (1.00 g, 3.86 mmol) in acetyl chloride (13.72 ml, 193 mmol, 50.0 equiv.) was stirred at 150° C. for 15 min. in a microwave. Upon completion of the reaction, the excess solvent was concentrated and dried to yield 740 mg of 6-bromoisochroman-1,3-dione as a white solid which was used as such without any further purification.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe excess solvent was concentrated
  3. customdried

Sources & evidence

ORD record
ord-b066951ecc0c48ceb104e3dfc82b0360
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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