1,2-Dibromoethane → 1-[2-(2-Bromoethoxy)-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Br:20][CH2:21][CH2:22]Br>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[Br:20][CH2:21][CH2:22][O:10][CH:9]=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
bis(3-Fluorophenyl)acetaldehyde (4.82 g, 0.0208 mol) was dissolved in dichloromethane (50 ml) and tetra-n-butyl ammonium bromide (0.67 g, 0.00208 mol) was added. 12 N sodium hydroxide solution (50 ml) and 1,2-dibromoethane (17.9 ml, 0.208 mol) were introduced and the mixture was stirred vigorously at room temperature for 20 h. Dichloromethane (100 ml) and saturated brine (50 ml) were added, and the phases were separated. The aqueous phase was extracted further with dichloromethane (50 ml) and the combined dichloromethane extracts were washed with water (2 × 75 ml) and saturated brine (50 ml). Drying of the dichloromethane solution (Na2SO4) and evaporation provided the title compound as an oil (6.66 g, 95%), TLC rf 0.71 (SiO2 dichloromethane).
Workup
- customthe phases were separated
- extractionThe aqueous phase was extracted further with dichloromethane (50 ml)
- washthe combined dichloromethane extracts were washed with water (2 × 75 ml) and saturated brine (50 ml)
- dry with materialDrying of the dichloromethane solution (Na2SO4) and evaporation
Sources & evidence
- ORD record
- ord-f759d033f8aa452788ff1c08be00369c
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05214057
Reaction notes
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