Methyl iodide → 2-(4-Bromo-2-fluorophenyl)-2-methylpropyl methyl ether

HRID 1438410ノート

反応式

HRID 1438410 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[C:4]([F:13])[CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:16][O:10][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:13])([CH3:11])[CH3:12]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 587623442-(4-Bromo-2-fluorophenyl)-2-methylpropan-1-ol

生成物 1

HCID 670472262-(4-Bromo-2-fluorophenyl)-2-methylpropyl methyl ether収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a DMF (4 ml) solution of 2-(4-bromo-2-fluorophenyl)-2-methylpropan-1-ol (199 mg, 0.8 mmol, WO2004074270A2) was added 60% sodium hydride (35 mg, 0.88 mmol) at 0° C. and the mixture was stirred at 0° C. for 15 minutes followed by additional stirring for 1 hour at room temperature. After the mixture was cooled to 0° C., methyliodide (342 mg, 2.4 mmol) was added and the mixture was stirred for 30 minutes at 0° C. followed by additional stirring for 16 hours at room temperature. Then, the reaction was quenched with water and the whole was extracted with EtOAc, which was dried over sodium sulfate. Then, filtration, evaporation and purification by silica gel column chromatography, eluting with hexane/EtOAc (20:1), gave the title compound (174 mg, 83% yield) as a colorless oil.

後処理

  1. stirringby additional stirring for 1 hour at room temperature
  2. temperatureAfter the mixture was cooled to 0° C.
  3. stirringthe mixture was stirred for 30 minutes at 0° C.
  4. stirringby additional stirring for 16 hours at room temperature
  5. customThen, the reaction was quenched with water
  6. extractionthe whole was extracted with EtOAc, which
  7. dry with materialwas dried over sodium sulfate
  8. filtrationThen, filtration, evaporation and purification by silica gel column chromatography
  9. washeluting with hexane/EtOAc (20:1)

出典と根拠

ORDレコード
ord-5bba1f4c8f314a07b9a9990ba8afbf87
出典データセット
uspto-grants-2009_11
特許番号
US07622589B2

反応ノート

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