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

HRID 53326Notes

Reaction equation

HRID 53326 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-6a363400835b4485b1a03f181c05d368
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

Loading…