4-Chlorophenol → HCID 9906124, 화합물

HRID 992482노트

반응식

HRID 992482 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([Mg]Br)C.[F:13][C:14]([F:27])([F:26])[C:15]1[CH:23]=[C:22]2[C:18]([C:19](=[O:25])[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:19]2([OH:25])[C:18]3[C:22](=[CH:23][C:15]([C:14]([F:27])([F:13])[F:26])=[CH:16][CH:17]=3)[NH:21][C:20]2=[O:24])[CH:3]=1

참가 물질

5

반응물 3

HCID 46844-ChlorophenolHCID 109876496-(trifluoromethyl)-2,3-dihydro-1H-indole-2,3-dioneHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 9906124HCID 9906124, 화합물수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-chlorophenol (2.87 g, 22.3 mmol) in THF (30 mL) at 0° C., 1.0 M solution of ethyl magnesium bromide (22.3 mL, 22.3 mmol) in THF was added dropwise. The resulting white suspension was then concentrated to dryness and dissolved in CH2Cl2 (30 mL). Neat 6-(trifluoromethyl)isatin (4.0 g, 18.6 mmol) was then added at once. After stirring at room temperature for 4 hours, the reaction was quenched with 1N HCl solution. The organic layer was separated, washed with water and brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo to provide a dark red oil which was purified by flash column chromatography (silica gel, 1:1 hexanes/EtOAc) to afford the title compound as an orange solid (5.48 g, 86% yield). 1H NMR (DMSO-d6): δ10.61 (s, 1H), 9.73 (s, 1H), 7.73(d, J=2.7 Hz, 1H), 7.15-7.21 (m, 2H), 7.03-7.07 (m, 2H), 6.81 (s, 1H), 6.61 (d, J=8.6 Hz, 1H).

후처리

  1. concentrationThe resulting white suspension was then concentrated to dryness
  2. dissolutiondissolved in CH2Cl2 (30 mL)
  3. customthe reaction was quenched with 1N HCl solution
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto provide a dark red oil which
  10. customwas purified by flash column chromatography (silica gel, 1:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-f98a5900b8854abbae80623f6d505771
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469042B1

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