Monoethyl malonate → Ethyl 3-(4-bromo-2-methylphenyl)-3-oxopropanoate

HRID 442797

Reaction equation

HRID 442797 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Li][Li].[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15]C(O)=O>>[CH3:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([CH2:15][C:14]([O:20][CH2:21][CH3:22])=[O:19])=[O:5]

Participants

4

Reactant 3

HCID 70615Monoethyl malonateHCID 139759Lithium, mol. (Li2)HCID 128464834-Bromo-2-methylbenzoyl chloride

Product 1

HCID 53404613Ethyl 3-(4-bromo-2-methylphenyl)-3-oxopropanoate

Procedure

2-Methyl-4-bromobenzoyl chloride (29.1 g, 0.13 mol) was treated with the dilithium salt of ethyl hydrogen malonate (28.0 g, 0.21 mol) and the product was isolated by the procedure described in Example 1 (ii). The crude product was purified on flash silica, eluting with dichloromethane-hexane (1:1 then 3:2) to give ethyl 2-methyl-4-bromobenzoylacetate as an oil.

Workup

  1. customthe product was isolated by the procedure
  2. customThe crude product was purified on flash silica
  3. washeluting with dichloromethane-hexane (1:1

Sources & evidence

ORD record
ord-ddc09ecaf6e64ae8b211449d5c77514a
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Linked notes

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