Dibromomethane → 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-ol

HRID 964733Notes

Reaction equation

HRID 964733 reaction equation
[CH3:1][CH:2]([CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[OH:6])[CH:3]=[CH2:4].Br[CH2:15]Br>CCOCC.[Zn].[Cu]Cl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([CH:5]([OH:6])[CH:2]([CH:3]2[CH2:15][CH2:4]2)[CH3:1])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 3024DibromomethaneHCID 113676051-(4-Chloro-phenyl)-2-methyl-but-3-en-1-ol

Product 1

HCID 190783851-(4-Chlorophenyl)-2-cyclopropylpropan-1-olYield 73%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

3-Methyl-4-(4-chlorophenyl)but-1-en-4-ol (63.68 g, approximately 90% pure, approximately 292 mmol), dibromomethane (45.5 ml, 648 mmol), zinc dust (84.75 g, 1.296 mol) and copper(I) chloride (12.83 g, 130 mmol) in dry ether (180 ml) were heated under reflux in a sonic bath for 31/2 hours. The mixture was then filtered (celite) and the filtrate poured into 2M hydrochloric acid. The mixture was extracted with ether and the combined extracts washed with water, saturated aqueous sodium bicarbonate solution and water, dried and evaporated in vacuo. Chromatography [SiO2, hexane-ethyl acetate (100:0) to (80:20)] gave 1-(4-chlorophenyl)-2-cyclopropylpropan-1-ol (44.72 g, 73%).

Workup

  1. temperatureunder reflux in a sonic bath for 31/2 hours
  2. filtrationThe mixture was then filtered (celite)
  3. additionthe filtrate poured into 2M hydrochloric acid
  4. extractionThe mixture was extracted with ether
  5. washthe combined extracts washed with water, saturated aqueous sodium bicarbonate solution and water
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a42d0a4547104423aafb481909f9e24c
Source dataset
uspto-grants-1998_06
Patent number
US05770741

Reaction notes

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