Ethyl bromoacetate → [1-Oxo-2-(2-chloroallyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

HRID 2083469Notes

Reaction equation

HRID 2083469 reaction equation
[Cl:1][C:2](=[CH2:18])[CH2:3][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].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28]>CN(C=O)C>[O:16]=[C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:13][CH2:26][C:27]([OH:29])=[O:28])=[C:8]([Cl:14])[C:7]=2[Cl:15])[CH2:12][C:4]1([CH2:3][C:2]([Cl:1])=[CH2:18])[CH3:17]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 203584572-(2-Chloroallyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone

Product 1

HCID 20358440[1-Oxo-2-(2-chloroallyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[1-Oxo-2-(2-chloroallyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid is prepared following substantially the same procedure described in Example 4, Step D, using the following reagents: 2-(2-chloroallyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (4.8 g., 0.0157 mole), potassium carbonate (6.0 g.), ethyl bromoacetate (4.5 ml.) and DMF (55 ml.). The above procedure gives 2.7 g. (48%) of [1-oxo-2-(2-chloroallyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which after recrystallization from butyl chloride melts at 160°-162° C.

Workup

  1. customThe above procedure gives 2.7 g
  2. custom(48%) of [1-oxo-2-(2-chloroallyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which after recrystallization from butyl chloride melts at 160°-162° C.

Sources & evidence

ORD record
ord-7df38bc167494fc7aaa8e8f28b47771d
Source dataset
uspto-grants-1978_04
Patent number
US04085219

Reaction notes

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