Tetrahydrofuran → 3-Chloro-2-(trifluoromethyl)phenylacetonitrile

HRID 1749489Notes

Reaction equation

HRID 1749489 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]([F:17])([F:16])[F:15])(=O)=O.C[Si](C)(C)[C:20]#[N:21].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(#N)C.O.C(OCC)(=O)C>[Cl:13][C:9]1[C:8]([C:14]([F:17])([F:16])[F:15])=[C:7]([CH2:6][C:20]#[N:21])[CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 1181621493-Chloro-2-(trifluoromethyl)benzyl methanesulfonate

Product 1

HCID 1181621683-Chloro-2-(trifluoromethyl)phenylacetonitrileYield 583.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-chloro-2-(trifluoromethyl)benzyl methanesulfonate (0.150 g, crude) and trimethylsilanecarbonitrile (119 mg, 1.2 mmol) in acetonitrile (5 mL) was added a solution of tetrabutylammonium fluoride in THF (1M, 1.2 mL, 1.2 mmol). The reaction was stirred at room temperature for 2 h. The reaction was treated with ethyl acetate and water, and the separated organic layer was washed with brine, dried and concentrated to give the crude product, which was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to afford the title compound (0.10 g, 3.03 mmol, 68% yield over three steps) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 7.56-7.48 (m, 3H), 3.99 (d, J=2.0 Hz, 2H).

Workup

  1. washthe separated organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0c9564ea0347453c81c33ceba4509fde
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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