[2-Bromo-4-(trifluoromethyl)benzyl]malonic acid → 3-(2-Bromo-4-(trifluoromethyl)phenyl)propanoic acid

HRID 2178754Notes

Reaction equation

HRID 2178754 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:3]=1[CH2:4][CH:5](C(O)=O)[C:6]([OH:8])=[O:7]>CCOCC>[Br:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 22754130[2-Bromo-4-(trifluoromethyl)benzyl]malonic acid

Product 1

HCID 227541293-(2-Bromo-4-(trifluoromethyl)phenyl)propanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

[2-Bromo-4-(trifluoromethyl)benzyl]malonic acid (9.80 g, 28.7 mmol) in a round-bottom flask was heated to 180° C. and heating was continued at 180° C. for 1.5 hrs. After cooling to room temperature, the solid was dissolved in ether. The resulting solution was dried over MgSO4 and concentrated. The solid was washed with hexane to give the title compound (7.20 g, 85%). MS calculated for C10H8BrF3O2: (M+H)+297; found 297.0, 299.0.

Workup

  1. temperatureheating
  2. dry with materialThe resulting solution was dried over MgSO4
  3. concentrationconcentrated
  4. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-5bb393760e0c41b481fb52ef83fce75f
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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