Potassium Iodide → Triethyl 2-[4-(trifluoromethoxy)phenyl]ethane-1,1,1-tricarboxylate

HRID 1256884Notes

Reaction equation

HRID 1256884 reaction equation
[CH:1]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([O:4][CH2:5][CH3:6])=[O:3].[F:17][C:18]([F:29])([F:28])[O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[F:17][C:18]([F:28])([F:29])[O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][C:1]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:2]([O:4][CH2:5][CH3:6])=[O:3])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 80471Triethyl methanetricarboxylateHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 68511908Triethyl 2-[4-(trifluoromethoxy)phenyl]ethane-1,1,1-tricarboxylateYield 100.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of triethyl methanetricarboxylate (4.55 g) in DMF (40 mL) were added 4-(trifluoromethoxy)benzyl bromide (5.00 g), potassium iodide in catalytic amount and potassium carbonate (4.07 g), and the mixture was stirred at room temperature for 3 hr. Ethyl acetate (200 mL) and water (100 mL) were added to extract the reaction mixture. The extract was washed sequentially with water and brine, and concentrated under reduced pressure to give the title compound (7.97 g) as an oil.

Workup

  1. extractionto extract the reaction mixture
  2. washThe extract was washed sequentially with water and brine
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f801f66264d84429acaf4c1228a48aaa
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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