Thionyl Chloride → HCID 22091453, compound

HRID 2229199Notes

Reaction equation

HRID 2229199 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([Cl:16])=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8](O)=[O:9].S(Cl)([Cl:19])=O>>[Cl:16][C:6]1[C:5]([O:4][CH2:3][CH2:2][Br:1])=[C:13]([O:14][CH3:15])[CH:12]=[CH:11][C:7]=1[C:8]([Cl:19])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22091452HCID 22091452, compound

Product 1

HCID 22091453HCID 22091453, compoundYield 100%

Conditions

Temperature
60 °C

Procedure

A suspension of 3-bromoethoxy-2-chloro-4-methoxybenzoic acid (1.4 g, 4.5 mmol) in thionyl chloride (20 ml) is heated at 60 ° C. until dissolved (˜20 min) plus an additional 30 minutes. The reaction mixture is cooled to room temperature and excess thionyl chloride is evaporated under reduced pressure. The resulting residue is evaporated at reduced pressure with toluene (50 ml) two times to obtain 1.5 g (100%) of 2-chloro-3-bromoethoxy-4-methoxybenzoic acid chloride.

Workup

  1. dissolutionuntil dissolved (˜20 min)
  2. customan additional 30 minutes
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customexcess thionyl chloride is evaporated under reduced pressure
  5. customThe resulting residue is evaporated at reduced pressure with toluene (50 ml) two times

Sources & evidence

ORD record
ord-d998379474bc4812a96d576dad345314
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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