2-Bromopropane → Methyl 2,4-dichloro-alpha-(1-methylethyl)benzeneacetate

HRID 745274Notes

Reaction equation

HRID 745274 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].Br[CH:17]([CH3:19])[CH3:18]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH:17]([CH3:19])[CH3:18])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 2734106Methyl 2,4-dichlorobenzeneacetate

Product 1

HCID 23315370Methyl 2,4-dichloro-alpha-(1-methylethyl)benzeneacetateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 22 parts of methyl 2,4-dichlorobenzeneacetate and 135 parts of N,N-dimethylformamide are added 3.1 parts of a sodium hydride dispersion 78% while nitrogen gas is introduced. After stirring till foaming has ceased, there are added 15 parts of 2-bromopropane and the whole is stirred for 3 hours at room temperature. The reaction mixture is poured onto water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed with water, dried, filtered and evaporated, yielding 24.5 parts (94%) of methyl 2,4-dichloro-α-(1-methylethyl)benzeneacetate as a residue.

Workup

  1. additionis introduced
  2. stirringthe whole is stirred for 3 hours at room temperature
  3. additionThe reaction mixture is poured onto water
  4. extractionthe product is extracted twice with 2,2'-oxybispropane
  5. washThe combined extracts are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4cd12ed9c4664e01bd3fec103c7abc26
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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