3-(Trifluoromethyl)benzoic acid → HCID 86614495, compound

HRID 250806Notes

Reaction equation

HRID 250806 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:26])=[O:25])[CH:19]=1.[F:29][C:30]1[C:35](O)=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40]>C1COCC1>[F:16][C:17]([F:27])([F:28])[C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[C:24]([O:26][C:35]1[C:34]([F:37])=[C:33]([F:38])[C:32]([F:39])=[C:31]([F:40])[C:30]=1[F:29])=[O:25]

Participants

5

Reactant 3

HCID 99633-(Trifluoromethyl)benzoic acidHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 86614495HCID 86614495, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N′-Dicyclohexylcarbodiimide (1.1 g, 5.3 mol) was added to a solution of α,α,α-trifluoro-m-toluic acid (1.0 g, 5.3 mmol) and pentafluorophenol (1.1 g, 5.8 mmol) in THF (10.0 mL). After stirring for 3.5 h, the solvent was removed under vacuum. The residue was dissolved in Et2O (20 mL), filtered, and washed with brine (2×10 mL), dried over Na2SO4, filtered, and evaporated to dryness to provide compound perfluorophenyl 3-(trifluoromethyl)benzoate as a yellow oil (1.7 g, 90%): 1H NMR (300 MHz, CD3OD) δ 8.51-8.39 (m, 2H), 8.09 (d, J=6.0 Hz, 1H), 7.88-7.79 (m, 1H); 19F NMR (282 MHz, CD3OD) δ −64.9 (3F), −155.6 (2F), −165.7 (1F), −168.9 (2F).

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in Et2O (20 mL)
  3. filtrationfiltered
  4. washwashed with brine (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c0e27d272b6549beb2a24c2b6c8e717d
Source dataset
uspto-grants-2011_01
Patent number
US07863317B2

Reaction notes

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