1,1-Dibromoethane → 1-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-ol

HRID 323808Notes

Reaction equation

HRID 323808 reaction equation
[Mg].BrC(Br)C.Br[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:17][CH2:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[Br:17][CH2:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]([OH:25])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 2596681-Bromo-4-phenylbutaneHCID 5462224MagnesiumHCID 110851354-(2-Bromoethyl)benzaldehyde

Product 1

HCID 221784871-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-olYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of magnesium (4.4 g) in tetrahydrofuran (20 ml) was added dibromoethane (1.6 ml) under a nitrogen atmosphere, and the mixture was stirred for 10 minutes. To the reaction mixture was added a solution of 1-bromo-4-phenylbutane (38.8 g) in tetrahydrofuran (30 ml) over 30 minutes, and the mixture was stirred for 40 minutes. The obtained Grignard reagent was dropwise added to a solution of 4-(2-bromoethyl)benzaldehyde (32.3 g) in tetrahydrofuran (250 ml) under ice-cooling over 30 minutes and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution (200 ml) under ice-cooling, and the mixture was extracted with ethyl acetate (200 ml). The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure to give a brown oily substance (70.5 g). The obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=10:1) to give 1-[4-(2-bromoethyl)phenyl]-5-phenylpentan-1-ol (32 g) as a yellow oily substance.

Workup

  1. stirringthe mixture was stirred for 40 minutes
  2. temperaturecooling over 30 minutes
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate (200 ml)
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customto give a brown oily substance (70.5 g)
  10. customThe obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ea1be48411ec487485576e18f01bbe75
Source dataset
uspto-grants-2001_04
Patent number
US06214873B1

Reaction notes

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