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

HRID 907256Notes

Reaction equation

HRID 907256 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>CC(C)=O>[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

4

Reactant 2

HCID 6367Acetyl chlorideHCID 534401324-Bromo-2-(carboxymethyl)benzoic acid2×

Product 1

HCID 217824866-Bromoisochroman-1,3-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-bromo-2-carboxymethyl-benzoic acid (product of step i)) (11.0 g) in acetone (200 mL) was treated with acetyl chloride (13.3 g) and the solution stirred at room temperature for 17 hours. The reaction mixture was evaporated then azeotroped with toluene to yield the sub-title compound (9.8 g).

Workup

  1. customThe reaction mixture was evaporated
  2. customthen azeotroped with toluene

Sources & evidence

ORD record
ord-653cc442b39f4443afe07810e18e60a5
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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