Ethyl bromoacetate → HCID 21483924, compound

HRID 1415210Notes

Reaction equation

HRID 1415210 reaction equation
[OH:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26]CC)=[O:25].[OH-].[K+]>CN(C=O)C.O.CO>[Cl:15][C:3]1[C:2]([O:1][CH2:23][C:24]([OH:26])=[O:25])=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]=2[C:4]=1[Cl:14]

Participants

8

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 21483890HCID 21483890, compound

Product 1

HCID 21483924HCID 21483924, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-3,4-dichloro-6,7,8,9-tetrahydro-5H- benzocyclohepten- 5-one (10 g., 0.04 mole), anhydrous potassium carbonate (7 g., 0.05 mole) and ethyl bromoacetate (8.35 g., 0.05 mole) in DMF (75 ml.) are stirred at 60° C. for 1 hour. Then potassium hydroxide (5 g.) dissolved in water (5 ml.) and methanol (100 ml.) is added. The mixture is refluxed for one hour. The methanol is distilled, the residue is poured into water, and the solution is filtered. Upon acidification with 12 N NCl, (3,4-dichloro-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten- 2-yloxy)acetic acid separates and is collected by filtration.

Workup

  1. temperatureThe mixture is refluxed for one hour
  2. distillationThe methanol is distilled
  3. additionthe residue is poured into water
  4. filtrationthe solution is filtered
  5. filtrationUpon acidification with 12 N NCl, (3,4-dichloro-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten- 2-yloxy)acetic acid separates and is collected by filtration

Sources & evidence

ORD record
ord-27757051d25f48ce8844a9214b38724b
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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