Dimethyl malate → 2-(2-Fluorobenzyloxy)-butane-1,4-dicarboxylic acid dimethyl ester

HRID 614697Notes

Reaction equation

HRID 614697 reaction equation
[CH3:1][O:2][C:3](=O)[CH:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])O.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1CBr>[Ag]=O.CCOCC>[CH3:10][O:9][C:7]([CH2:6][CH:3]([O:2][CH2:1][C:20]1[CH:19]=[CH:18][CH:17]=[CH:14][C:13]=1[F:12])[CH2:4][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:8]

Participants

5

Reactant 2

HCID 12674Dimethyl malateHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 538170452-(2-Fluorobenzyloxy)-butane-1,4-dicarboxylic acid dimethyl esterYield 131.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

46.4 g (0.2 mol) of silver oxide were added in portions, with constant stirring, to a mixture of 16.2 g (0.1 mol) of malic acid dimethyl ester and 57 g (0.30 mol) of 2-fluorobenzyl bromide. An exothermic reaction started slowly, and the temperature rose to 80° C. After cooling, 200 ml of ether were added, the solid was filtered off, the filtrate was concentrated and the residue was distilled at 180° C. in a waterpump vacuum. 19.6 g (72.6% of theory) of 2-(2-fluorobenzyloxy)-butane-1,4-dicarboxylic acid dimethyl ester were obtained.

Workup

  1. customAn exothermic reaction
  2. customrose to 80° C
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. distillationthe residue was distilled at 180° C. in a waterpump vacuum

Sources & evidence

ORD record
ord-ea16179e746c48efbbe5562a88865ebe
Source dataset
uspto-grants-1979_03
Patent number
US04146384

Reaction notes

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