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

HRID 1749489노트

반응식

HRID 1749489 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0c9564ea0347453c81c33ceba4509fde
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156798B2

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