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

HRID 1515541ノート

反応式

HRID 1515541 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 591917922-(Cyclopropylthio)-5-nitrobenzaldehyde

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 21868444Ether tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e0c576c4924f403484ed1338e3426851
出典データセット
uspto-grants-2012_07
特許番号
US08222453B2

反応ノート

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