Ethyl bromoacetate → HCID 12395597, compound

HRID 1287433Notes

Reaction equation

HRID 1287433 reaction equation
[CH2:1]([C:4]1([CH3:17])[CH2:12][C:11]2[C:6](=[C:7]([Cl:15])[C:8]([Cl:14])=[C:9]([OH:13])[CH:10]=2)[C:5]1=[O:16])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+]>CN(C=O)C.O>[O:16]=[C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:13][CH2:25][C:26]([OH:28])=[O:27])=[C:8]([Cl:14])[C:7]=2[Cl:15])[CH2:12][C:4]1([CH2:1][CH:2]=[CH2:3])[CH3:17]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12395592HCID 12395592, compound

Product 1

HCID 12395597HCID 12395597, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 2-allyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (3.4 g, 0.0126 mole), potassium carbonate (4.2 g.) and ethyl bromoacetate (4.8 g.) in DMF (40 ml.) is warmed at 55° C. in an inert atmosphere, then treated with water (40 ml.) and 10N sodium hydroxide (2 ml.) and heated on a steam bath for one hour, poured into water (300 ml.), acidified and extracted with ether. The ether extract is washed with water, dried over magnesium sulfate and the solvent evaporated to leave a tan oil which is purified by chromatography over silica affording 2.0 g. of (1-oxo-2-allyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid as a tan oil.

Workup

  1. temperatureheated on a steam bath for one hour
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated
  7. customto leave a tan oil which
  8. customis purified by chromatography over silica affording 2.0 g

Sources & evidence

ORD record
ord-7fea45c4e5a141289ef486696b3155ef
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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