Potassium Carbonate → 2-(Cyclopropylthio)-5-nitrobenzaldehyde

HRID 1515541노트

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HRID 1515541 반응식
[CH:1]1([SH:4])[CH2:3][CH2:2]1.F[C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=1[CH:8]=[O:9].C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(OCC)C.CN(C=O)C.CCOC(C)=O>[CH:1]1([S:4][C:6]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=2[CH:8]=[O:9])[CH2:3][CH2:2]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27347702-Fluoro-5-nitrobenzaldehydeHCID 4713099Cyclopropanethiol

생성물 1

HCID 591917922-(Cyclopropylthio)-5-nitrobenzaldehyde

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 21868444Ether tetrahydrofuran용매

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온도
45 °C

실험 절차

Freshly prepared cyclopropyl thiol in THF/diethyl ether (J. Am. Chem. Soc. 1992, 114(9), 3497) was added to 2-fluoro-5-nitrobenzaldehyde (3.4 g, 20 mmol, 1.0 eq.) and K2CO3 (4.83 g, 35 mmol) in DMF (20 mL). The mixture was stirred at 45° C. for 1.0 h and at rt over night. It was diluted with EtOAc and washed with water. The aqueous was extracted with EtOAc and the combined organic layers were washed with brine and dried over Na2SO4. After evaporation of solvent, the crude was tritutated with EtOAc/hexanes (70/120). The solid was collected to give 76A (3.2 g). The filtrate was condensed and triturated again to give a second crop of 76A (0.5 g, total yield 85%). 1H NMR (400 MHz, CDCl3) δ ppm 0.74-0.83 (m, 2H) 1.20-1.28 (m, 2H) 2.13-2.19 (m, 1H) 7.95 (d, J=9.23 Hz, 1H) 8.33 (dd, J=8.79, 2.64 Hz, 1H) 8.62 (d, J=2.64 Hz, 1H) 10.15 (s, 1H).

후처리

  1. washwashed with water
  2. extractionThe aqueous was extracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation of solvent
  6. customThe solid was collected

출처 및 근거

ORD 기록
ord-e0c576c4924f403484ed1338e3426851
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222453B2

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