Water → (3-Bromophenyl)(4-methylphenyl)methanone

HRID 45480ノート

反応式

HRID 45480 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[Br:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[C:18](N(C)C)=[O:19].O>C1COCC1.CCCCC>[Br:14][C:15]1[CH:16]=[C:17]([C:18]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[O:19])[CH:23]=[CH:24][CH:25]=1

参加物

7

反応物 4

HCID 962WaterHCID 78054-BromotolueneHCID 33358263-bromo-N,N-dimethylbenzamideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 2757054(3-Bromophenyl)(4-methylphenyl)methanone収率 83%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-80 °C

実験手順

To a solution of 38.5 g (0.225 mol) of 4-bromotoluene in 450 mL of THF, 300 mL (0.450 mol) of 1.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 hr at −80° C. This mixture was slowly warmed to room temperature and additionally stirred at this temperature for 30 min. To this mixture 52.0 g (0.23 mol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and then this mixture was stirred for 12 hr at room temperature. Later, 300 mL of water was added, organic solvent was evaporated using a rotary evaporator. The product was extracted with 2×200 mL of dichloromethane. The combined organic extracts were evaporated to dryness, and the residue was dried in vacuum. This procedure gave 51.3 g (83%) of 40 which was further used without additional purification.

後処理

  1. temperatureThis mixture was slowly warmed to room temperature
  2. stirringadditionally stirred at this temperature for 30 min
  3. stirringthis mixture was stirred for 12 hr at room temperature
  4. customorganic solvent was evaporated
  5. customa rotary evaporator
  6. extractionThe product was extracted with 2×200 mL of dichloromethane
  7. customThe combined organic extracts were evaporated to dryness
  8. customthe residue was dried in vacuum

出典と根拠

ORDレコード
ord-559d82a387544e008795df8e74291c68
出典データセット
uspto-grants-2013_09
特許番号
US08541522B2

反応ノート

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