Dimethylformamide → Ethyl 7-(3,5-bis(trifluoromethyl)phenoxy)heptanoate

HRID 1363874Notes

Reaction equation

HRID 1363874 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[F:13][C:14]([F:27])([F:26])[C:15]1[CH:16]=[C:17]([OH:25])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[F:13][C:14]([F:26])([F:27])[C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1)[O:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 676803,5-Bis(trifluoromethyl)phenolHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 86620562Ethyl 7-(3,5-bis(trifluoromethyl)phenoxy)heptanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 7-bromoheptanoate and 3,5-bis(trifluoromethyl) phenol were added to dimethylformamide (DMF). The solution was added with potassium carbonate and stirred at room temperature. The solution was added with water and extracted twice with ethyl acetate. After the organic layer was washed three times with water and dried over anhydrous magnesium sulfate, the solvent was removed. The residue was purified by silica gel column chromatography to obtain ethyl 7-(3,5-bis (trifluoromethyl)phenoxy)heptanoate.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washAfter the organic layer was washed three times with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8e04a83780f4898b380de6ef251f5f6
Source dataset
uspto-grants-2011_02
Patent number
US07887835B2

Reaction notes

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