Dimethylformamide → 3-Bromo-5-[1-(4-fluorophenyl)-1-hydroxyethyl]-benzaldehyde

HRID 53326ノート

反応式

HRID 53326 の反応式
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([CH3:16])[OH:15])[CH:10]=[C:11]([Br:13])[CH:12]=1.CN(C)[CH:26]=[O:27]>CCCCCC.C(OCC)C>[Br:13][C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([C:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([OH:15])[CH3:16])[CH:10]=1)[CH:26]=[O:27]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 199624103,5-Dibromo-alpha-(4-fluorophenyl)-alpha-methylbenzenemethanolHCID 178418339Butyllithium

生成物 1

HCID 199623993-Bromo-5-[1-(4-fluorophenyl)-1-hydroxyethyl]-benzaldehyde収率 41.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

A 2.5M solution of n-butyllithium in hexane (10.7 ml) was added dropwise to a stirred suspension of 3,5-dibromo-α-(4-fluorophenyl)-α-methylbenzenemethanol (5.90 g) in dry diethyl ether (160 ml) at -78° C. under an atmosphere of dry nitrogen. The resulting mixture was stirred at this temperature for 30 minutes and then N,N-dimethylformamide (2.93 g) was added dropwise. Stirring at -78° C. was continued for 1 hour and then the reaction was quenched by the addition of water. The temperature was allowed to reach room temperature and the organic layer was separated, washed with water and dried (MgSO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution was commenced with hexane/dichloromethane (1:1), and the ratio was gradually changed to hexane/dichloromethane (1:5). The later product fractions were combined and evaporated to give the title compound as an oil (2.10 g), Rf 0.15 (SS 1). Found: C,55.39; H,3.78. C15H12BrO2F requires C,55.75; H,3.74%.

後処理

  1. stirringStirring at -78° C.
  2. waitwas continued for 1 hour
  3. customthe reaction was quenched by the addition of water
  4. customto reach room temperature
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customEvaporation of the solvent
  9. customgave an oil which
  10. customwas chromatographed on silica gel
  11. washElution
  12. customevaporated

出典と根拠

ORDレコード
ord-6a363400835b4485b1a03f181c05d368
出典データセット
uspto-grants-1997_04
特許番号
US05618941

反応ノート

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