Benzyl Alcohol → 3-(Trifluoromethyl)-4-(benzyloxy)nitrobenzene

HRID 51105ノート

反応式

HRID 51105 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24]>CN(C=O)C>[CH2:3]([O:10][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[C:23]([F:24])([F:25])[F:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 219520843-(Trifluoromethyl)-4-(benzyloxy)nitrobenzene収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

60% NaH dispersion (1.4 g, 33.5 mmol) in mineral oil was washed with hexanes and then suspended in DMF (10 ml). To this NaH suspension in DMF, added benzyl alcohol (2.8 ml, 26.3 mmol) with water bath to keep the temperature below 30 ° C. The reaction mixture was stirred until the evolution of the hydrogen gas ceased. To a solution of 2-fluoro-5-nitrobenzotrifluoride (5.0 g, 23.9 mmol) in DMF (20 ml) was added the benzyl alkoxide solution slowly at 0 ° C. Upon the completion of the addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 200 ml ice water, stirred until the yellow solid was formed. Filtered and the solid was washed with water and then trituated with pentane. 5.9 g yellow solid was collected (yield: 83%). ESI-MS m/z 298 (M+H)+.

後処理

  1. wash60% NaH dispersion (1.4 g, 33.5 mmol) in mineral oil was washed with hexanes
  2. customthe temperature below 30 ° C
  3. additionUpon the completion of the addition
  4. customthe ice bath was removed
  5. additionThe reaction mixture was poured into 200 ml ice water
  6. stirringstirred until the yellow solid
  7. customwas formed
  8. filtrationFiltered
  9. washthe solid was washed with water
  10. custom5.9 g yellow solid was collected (yield: 83%)

出典と根拠

ORDレコード
ord-d1fa74d56fc34419a16a521e6bcb4366
出典データセット
uspto-grants-2004_03
特許番号
US06713485B2

反応ノート

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