Bromine → HCID 13042092, compound

HRID 67860Notes

Reaction equation

HRID 67860 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:9][C:8]=1[Cl:17])C.[Br:19]Br>CO.Cl>[Cl:17][C:8]1[CH:9]=[C:10]([C:13](=[O:16])[CH:14]([Br:19])[CH3:15])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([O:3][CH3:1])=[O:18]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 11608739Ethyl-2-(2-chloro-4-propionylphenoxy)acetate

Product 1

HCID 13042092HCID 13042092, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

Ethyl-2-(2-chloro-4-propionylphenoxy)acetate(4 g) was dissolved in methanol (40-50 ml). HCl (2 drops, conc) was added, followed by the dropwise addition over 5-10 minutes of bromine (2.62 g, 0.016 mole). After the bromine addition was complete the mixture was heated on a steam bath for 15-30 minutes allowing much of the solvent to evaporate. The residue was washed with cold water and the remaining solid recrystallized several times from hexane to give methyl 2-[2-chloro-4-(2-bromopropionyl)phenoxy]acetate (4.6 g, 90%, mp 63°-65° C.

Workup

  1. temperaturewas heated on a steam bath for 15-30 minutes
  2. customto evaporate
  3. washThe residue was washed with cold water
  4. customthe remaining solid recrystallized several times from hexane

Sources & evidence

ORD record
ord-43bab90c33a24769acef8896218c52fe
Source dataset
uspto-grants-1982_08
Patent number
US04347178

Reaction notes

Loading…