Trifluoroacetic acid → {2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid

HRID 852366Notes

Reaction equation

HRID 852366 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:11][C:10]=1[CH3:29])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:29][C:10]1[CH:11]=[C:12]([S:15][CH2:16][C:17]#[C:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=2)[CH:13]=[CH:14][C:9]=1[O:8][CH2:7][C:6]([OH:30])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69458063{2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester

Product 1

HCID 11696577{2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 75 mg (1.7 mmol) of the above prepared {2-methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester in 2 ml dichloromethane was treated at 0° C. with 0.4 ml TFA and stirred at RT for 3 h. The reaction was evaporated, dissolved in toluene and evaporated again (two times). Purification by flash chromatography on SiO2 with a gradient of CH2Cl2/MeOH (98:2 to 9:1) yielded 30 mg of the title compound as white crystals, mp. 130-131° C.

Workup

  1. customThe reaction was evaporated
  2. dissolutiondissolved in toluene
  3. customevaporated again (two times)
  4. customPurification by flash chromatography on SiO2 with a gradient of CH2Cl2/MeOH (98:2 to 9:1)

Sources & evidence

ORD record
ord-d8f43f492d204df3a52bd368a7d1eae5
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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