1,3,5-Tribromobenzene → 3,5-Dibromo-alpha-(4-fluorophenyl)benzenemethanol

HRID 53323

반응식

HRID 53323 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([Br:14])[CH:8]=1.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1>CCCCCC.CCOCC>[Br:14][C:9]1[CH:8]=[C:7]([CH:20]([C:19]2[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=2)[OH:21])[CH:12]=[C:11]([Br:13])[CH:10]=1

참가 물질

6

반응물 3

HCID 122791,3,5-TribromobenzeneHCID 680234-FluorobenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 199623533,5-Dibromo-alpha-(4-fluorophenyl)benzenemethanol수율 87.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

A 2.5M solution of n-butyllithium in hexane (44.0 ml) was added dropwise to a stirred suspension of 1,3,5-tribromobenzene (31.5 g) in dry ether (1000 ml) at -78° C. under an atmosphere of dry nitrogen. The resulting mixture was stirred at this temperature for 30 minutes and the 4-fluorobenzaldehyde (13.65 g) was added dropwise. Stirring at -78° C. was continued for a further 30 minutes 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 and dried (MgSO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. The column was eluted with dichloromethane/hexane (1:5), gradually increasing the ratio of solvents to 2:3. The product fractions were combined, evaporated and the residue was triturated with hexane to give the title compound (31.42 g), m.p. 92°-93° C. Found: C,43.75; H,2.43. C13H9Br2OF requires C,43.37; H,2.52%.

후처리

  1. stirringStirring at -78° C.
  2. waitwas continued for a further 30 minutes
  3. customthe reaction was quenched by the addition of water
  4. customto reach room temperature
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customwas chromatographed on silica gel
  10. washThe column was eluted with dichloromethane/hexane (1:5)
  11. temperaturegradually increasing the ratio of solvents to 2:3
  12. customevaporated
  13. customthe residue was triturated with hexane

출처 및 근거

ORD 기록
ord-b4e48c84258f420eb82815a11ed661a9
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618941

연결된 노트

불러오는 중…