Dicyclohexylcarbodiimide → 2-Phenoxy-benzoic acid 3,5-bis-trifluoromethyl-benzyl ester

HRID 2186783Notes

Reaction equation

HRID 2186783 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22]O.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[F:17][C:18]([F:31])([F:32])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[CH2:22][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 752372-Phenoxybenzoic acidHCID 1229333,5-Bis(trifluoromethyl)benzyl alcohol

Product 1

HCID 98460672-Phenoxy-benzoic acid 3,5-bis-trifluoromethyl-benzyl esterYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 118 mg (0.55 mmol) 2-phenoxybenzoic acid and 122 mg (0.50 mmol) 3,5 bis(trifluoromethyl)benzyl alcohol in 1.5 ml dichloromethane at 0° C. was added a solution of 124 mg (0.60 mmol) 1,3-dicyclohexylcarbodiimide and 7 mg (0.06 mmol) 4-dimethylaminopyridine in 1 ml dichloromethane. The ice bath was removed and stirring was continued at room temperature overnight. The solvent was removed in vacuo and the residue re-dissolved in diethyl ether, filtered and evaporated. The residue was purified by flash chromatography to give 70 mg (32%) of the title compound as white crystals.

Workup

  1. customThe ice bath was removed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue re-dissolved in diethyl ether
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e937365a4b254fdc8136a13598b5e718
Source dataset
uspto-grants-2002_06
Patent number
US06407111B1

Reaction notes

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