Ethyl bromoacetate → 14738-27-3

HRID 6690

반응식

HRID 6690 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:13][C:14](=[O:17])[CH2:15]Br)[CH3:12]>C1COCC1>[CH2:11]([O:13][C:14](=[O:17])[CH2:15][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:12]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 78114-MethylbenzenethiolHCID 24758Sodium hydride

생성물 1

HCID 27149214738-27-3수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for 3 h. The solvent was removed under vacuum. The residue was dissolved in oil. HCl and extracted by ethylacetate. The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine then dried over Na2SO4. Evaporation of organic phase yielded 8.46 g (99%) colorless oil. 1H NMR (CDCl3): δ 1.22 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.57 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H). EIMS m/z 210 (M+1), 233 (M+23).

후처리

  1. stirringfurther stirred at room temperature for 3 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in oil
  4. extractionHCl and extracted by ethylacetate
  5. washThe combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
  6. dry with materialthen dried over Na2SO4
  7. customEvaporation of organic phase

출처 및 근거

ORD 기록
ord-303d0064dc364a3489dbbedaa84ff1ac
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084141B2

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