Acetic Acid → HCID 19598109, compound

HRID 611708Notes

Reaction equation

HRID 611708 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][CH:3]=1.[Br:15]Br.C(O)(=O)C>O>[Br:15][C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([C:2]=1[Cl:1])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 15192436HCID 15192436, compound

Product 1

HCID 19598109HCID 19598109, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 6-chloro-2-methoxybenzoate (1.8 g, 8.4 mmol), bromine (1.41 g, 8.8 mmol) and acetic acid (5 ml) is stirred at room temperature for 24 hours. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is separated and concentrated and the residue is purified by column chromatography (petrol ether:ethyl acetate, 95:5 v/v) yielding the pure product as a yellow oil, 1.7 g, (69%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated
  3. concentrationconcentrated
  4. customthe residue is purified by column chromatography (petrol ether:ethyl acetate, 95:5 v/v)

Sources & evidence

ORD record
ord-aac4d56e9c0642dba27ca5934aca38e7
Source dataset
uspto-grants-1999_12
Patent number
US06001883

Reaction notes

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