1,2-Dibromoethane → 1-[2-(2-Bromoethoxy)-1-(2-methylphenyl)ethenyl]-4-fluoro-2-methylbenzene

HRID 1460660Notes

Reaction equation

HRID 1460660 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:9]=[O:10])=[C:4]([CH3:18])[CH:3]=1.[H-].[Na+].[Br:21][CH2:22][CH2:23]Br>C1COCC1>[Br:21][CH2:22][CH2:23][O:10][CH:9]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 53922880(4-Fluoro-2-methylphenyl)-(2-methylphenyl)acetaldehyde

Product 1

HCID 542963141-[2-(2-Bromoethoxy)-1-(2-methylphenyl)ethenyl]-4-fluoro-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(4-Fluoro-2-methylphenyl)-(2-methylphenyl)acetaldehyde (3.5 g, 0.0444 mol) was dissolved in dry THF (20 ml) and added dropwise to a suspension of sodium hydride (60% oil dispersion) (0.63 g, 0.0158 mol) in dry tetrahydrofuran (30 ml). The mixture was stirred at room temperature for 1 h and heated at reflux for 0.5 h. After cooling 1,2-dibromoethane (12.4 ml, 10 equiv.) was added, and the reaction mixture was allowed to stand at room temperature for 192 h. The reaction mixture was filtered and evaporated. The residue was pumped in vacuo, but still contained ca. 30% starting aldehyde, so the above procedure was repeated.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 h
  3. additionwas added
  4. waitto stand at room temperature for 192 h
  5. filtrationThe reaction mixture was filtered
  6. customevaporated

Sources & evidence

ORD record
ord-fe3cb37d64b14e26b02f11756fee37a8
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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