4-Toluenesulfonyl chloride → (2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-tosyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

HRID 1607365Notes

Reaction equation

HRID 1607365 reaction equation
[CH3:1][C:2]1([CH3:31])[CH:4]([CH:5]([OH:13])[C:6]([Cl:12])([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]=1[CH3:30])=[O:15].[H-].[Na+].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.[Cl-].[NH4+]>C(OCC)C.CN(C=O)C>[CH3:1][C:2]1([CH3:31])[CH:4]([CH:5]([O:13][S:40]([C:37]2[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=2)(=[O:42])=[O:41])[C:6]([Cl:11])([Cl:12])[C:7]([F:8])([F:10])[F:9])[CH:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]=1[CH3:30])=[O:15]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13933697(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxyl-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

Product 1

HCID 13956723(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-tosyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylateYield 65.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 97 mg (0.20 mmol) of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 3 and dissolved in 0.5 ml of diethyl ether and 0.5 ml of DMF, 12 mg (0.25 mmol) of sodium hydride and 39 mg (0.20 mmol) of p-toluenesulfonyl chloride were added, and the mixture was stirred overnight at room temperature. After an addition of 1 ml of a saturated ammonium chloride aqueous solution, the mixture was extracted with diethyl ether (2 ml×3 times). The extract was dried over anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure to obtain a crude produce. The crude product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/3) to obtain 83 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-tosyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate as a colorless oily substance.

Workup

  1. extractionthe mixture was extracted with diethyl ether (2 ml×3 times)
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a crude
  6. customproduce
  7. customThe crude product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/3)

Sources & evidence

ORD record
ord-2a6a4fac549f4792a6df50265e8c39d9
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Reaction notes

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