Hydrochloric Acid → 4-Cyclopentyl-3-(trifluoromethyl)benzonitrile

HRID 217471

반응식

HRID 217471 반응식
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].CN1CCCC1=O.[CH:21]1([Mg]Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl>C1COCC1.C(OCC)C.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[CH:21]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:13])([F:12])[F:11])[CH2:25][CH2:24][CH2:23][CH2:22]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 27364744-Chloro-3-(trifluoromethyl)benzonitrileHCID 178419650HCID 178419650, 화합물

생성물 1

HCID 592144344-Cyclopentyl-3-(trifluoromethyl)benzonitrile

시약·촉매·용매 3

HCID 11110968Iron (III) acetylacetonate촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-chloro-3-(trifluoromethyl)benzonitrile (1.5 g), iron (III) acetylacetonate (130 mg), and 1-methylpyrrolidin-2-one (4 mL) in THF (45 mL) was added a 1 M solution of cyclopentyl magnesium bromide in THF (8.8 mL) at 5° C., followed by stirring at room temperature for 0.5 hours and diluting with diethylether. 1 M hydrochloric acid was slowly added thereto, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 95:5) to obtain 4-cyclopentyl-3-(trifluoromethyl)benzonitrile (367 mg) as a white solid.

후처리

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 95:5)

출처 및 근거

ORD 기록
ord-35b866f798f740aebaad3a0c86cb4316
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193378B2

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