Ethyl Acetate → 2-Bromo-1-[(2,2-diethoxyethyl)thio]-4-chlorobenzene

HRID 2199694ノート

反応式

HRID 2199694 の反応式
C(=O)([O-])[O-].[K+].[K+].CO[CH:9](OC)[CH2:10]Br.[Br:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[SH:22].[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>CN(C=O)C.O>[Br:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[S:22][CH2:24][CH:23]([O:25][CH2:9][CH3:10])[O:26][CH2:27][CH3:28]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 218168372-Bromo-4-chlorobenzene-1-thiol

生成物 1

HCID 670034092-Bromo-1-[(2,2-diethoxyethyl)thio]-4-chlorobenzene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Potassium carbonate (0.926 g, 9.34 mmol) then bromoacetaldehyde dimethyl acetal (1.35 g, 6.85 mmol) were added to a solution of 2-bromo-4-chlorobenzenethiol (1.397 g, 6.23 mmol) in anhydrous DMF (11 mL). The mixture was heated at 70° C. for 3 hours. After being allowed to cool to room temperature, the mixture was diluted with ethyl acetate and water. The resulting layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organics were washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The resulting light yellow oil was used directly for the following step. 1H NMR (500 MHz, CDCl3) δ 7.57 (d, J=2.0 Hz, 1H); 7.33 (d, J=8.5 Hz, 1H); 7.26 (dd, J=8.5, 2.0 Hz, 1H); 4.70 (t, J=5.5 Hz, 1H); 3.75-3.68 (m, 2H); 3.61-3.55 (m, 2H); 3.15 (d, J=5.5 Hz, 2H); 1.23 (t, 7.0 Hz, 6H).

後処理

  1. temperatureto cool to room temperature
  2. customThe resulting layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organics were washed with water
  5. dry with materialsaturated NaCl (aq), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-243693533667479381d774eb63432a1f
出典データセット
uspto-grants-2016_06
特許番号
US09359339B2

反応ノート

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