Diethyl octylmalonate → HCID 86758611, compound

HRID 1018881Notes

Reaction equation

HRID 1018881 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.C([O-])C.[Na+].[CH2:15]([O:17][C:18](=[O:33])[CH:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16]>C(O)C>[CH2:15]([O:17][C:18](=[O:33])[C:19]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][C:4]=1[F:10])([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16]

Participants

5

Reactant 3

HCID 252340Diethyl octylmalonateHCID 2723922Sodium ethoxideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 86758611HCID 86758611, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-bromo-2-fluoro-benzylbromide [76283-09-5] is reacted in ethanol with stoichiometric compounds of natrium ethanolate and octylmalonic acid diethylester to form 2-(4-bromo-2-fluoro phenyl)methyl-2-octyl malonic acid diethylester. After usual post-treatment and distillation a 50% aqueous potassium hydroxide solution is added to the methanolic solution and heated until the saponification has ended. After cooling sulfuric acid is added to adjust the pH to a value of 1-2. The 4-fold volume of water is added followed by multiple extraction of methyl-tert.-butylether. The combined organic phases are dried and the solvent is removed under vacuum, finally at 60° C. in the heating bath. The 2-(4-bromo-2-fluoro phenyl)methyl-2-octyl-malonic acid thus obtained after heating for several hours at 150-170° C. is decarboxylated to obtain 3-(4-bromo-2-fluoro phenyl)-2-octyl-propionic acid.

Sources & evidence

ORD record
ord-0c3cf4d68a164c7baa426b546a14e008
Source dataset
uspto-grants-2002_11
Patent number
US06485797B1

Reaction notes

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