Water → 2-Chloro-3-(trifluoromethyl)benzaldehyde

HRID 1096833

反応式

HRID 1096833 の反応式
[Li]CCCC.[F:6][C:7]([F:16])([F:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].CN([CH:20]=[O:21])C.O>C1COCC1>[Cl:14][C:9]1[C:8]([C:7]([F:6])([F:15])[F:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:20]=[O:21]

参加物

6

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 69211-Chloro-2-(trifluoromethyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 27366722-Chloro-3-(trifluoromethyl)benzaldehyde収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

BuLi (1.6 M in hexane, 173 mL, 277 mmol) was added to a sol. of 2-trifluoromethyl-chlorobenzene (50.0 g, 277 mmol) in THF (500 mL) at −70° C. The sol. was stirred for 2 h at −70° C., and DMF (21.3 mL, 277 mmol) in THF (100 mL) was added. The mixture was allowed to warm to rt overnight. Water was added (200 mL), and the mixture was extracted with Et2O (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 20:1) yielded the title compound (37.4 g, 65%). LC-MS: tR=0.96 min.

後処理

  1. temperatureto warm to rt overnight
  2. extractionthe mixture was extracted with Et2O (2×)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (heptane/EtOAc 20:1)

出典と根拠

ORDレコード
ord-43cb4c74db514d84b642b57af4708b1f
出典データセット
uspto-grants-2012_03
特許番号
US08138340B2

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