Hydrochloric Acid → {2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester

HRID 852365Notes

Reaction equation

HRID 852365 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]#[CH:18])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2].I[C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1.CCN(CC)CC.Cl>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CCOCC>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]#[C:18][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 86602538(2-Methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 69458063{2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl esterYield 52.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A degassed (argon) solution of 96.0 mg (0.33 mmol) (2-methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester, 0.053 ml (0.36 mmol) 1-iodo-4-trifluoromethyl-benzene and 0.086 (0.621 mmol) Et3N in 1 ml DMF was treated with 37.9 mg (0.03 mmol) Pd(PPh3)4 and 12.5 mg (0.07 mmol) of CuI. After stirring for 2 h at room temperature, the reaction was distributed between 1N HCl and ether (three times). Washing of the organic layer with saturated aqueous NH4Cl solution and brine, drying (Na2SO4) and evaporation of the solvents, followed by flash chromatography (SiO2, n-heptane/EtOAc 1 to 5%), yielded 76 mg of the title compound as yellow oil.

Workup

  1. washWashing of the organic layer with saturated aqueous NH4Cl solution and brine
  2. customdrying
  3. custom(Na2SO4) and evaporation of the solvents

Sources & evidence

ORD record
ord-b304c27d0097490cb727dbc9e1390786
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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