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

HRID 2199694노트

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HRID 2199694 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-243693533667479381d774eb63432a1f
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359339B2

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