Hydrochloric Acid → 1-(2-Bromo-ethoxy)-2-methoxy-4-methyl-benzene

HRID 734401

반응식

HRID 734401 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10].[H-].[Na+].[Br:13][CH2:14][CH2:15]Br.Cl>CN(C=O)C>[Br:13][CH2:14][CH2:15][O:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[O:2][CH3:1]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 71442-Methoxy-4-MethylphenolHCID 78391,2-DibromoethaneHCID 24758Sodium hydride

생성물 1

HCID 246891991-(2-Bromo-ethoxy)-2-methoxy-4-methyl-benzene수율 25.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 2-methoxy-4-methylphenol (1000 mg, 7.24 mmol) in DMF (40 mL) at rt was added sodium hydride (60% dispersion in mineral oil, 579 mg, 14.48 mmol). The reaction mixture was stirred for 1 h, then 1,2-dibromoethane (6.80 g, 136.18 mmol) was added. The resulting solution was heated at 50° C. for 24 h, then cooled to rt. The solution was treated with 2N HCl and extracted with EtOAc. The combined extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography using a step gradient of 30 and 50% EtOAc/hexanes to give the title compound as a white solid (460 mg, 24%). GC/MS (EI) m/z 244 (M)+, RT 7.40 min.

후처리

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2015f34f08bf4d0b87f94842d4580eef
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592361B2

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