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

HRID 734401

反応式

HRID 734401 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2015f34f08bf4d0b87f94842d4580eef
出典データセット
uspto-grants-2009_09
特許番号
US07592361B2

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