Diethyl Ether → 1-(2-Chlorophenyl)-2-(4-chlorophenyl)ethanone

HRID 916975Notes

Reaction equation

HRID 916975 reaction equation
[Mg].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#N.CC[O:22]CC>>[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14](=[O:22])[CH2:7][C:6]1[CH:9]=[CH:10][C:3]([Cl:2])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether4×HCID 133912-ChlorobenzonitrileHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5462224Magnesium

Product 1

HCID 3483121-(2-Chlorophenyl)-2-(4-chlorophenyl)ethanone

Conditions

Temperature
34 °C

Procedure

To a dried three-neck round bottom flask fitted with a condenser and addition funnel was added magnesium (2.217 g, 91.2 mmol) and anhydrous ether (60 mL). A solution of 4-chlorobenzyl bromide (18.74 g, 91.2 mmol) in ether (100 mL) was added dropwise via the addition funnel at room temperature. After the addition, the reaction mixture was heated at 34° C. for 1 hour. The reaction mixture was allowed to cool to room temperature. One half of the volume of the ether solution was then added to another dried flask charged with a solution of 2-chlorobenzonitrile (5.228 g, 38.0 mmol) in ether (70 mL). The resulting reaction mixture was stirred at 34° C. for 3 hours. The reaction was cooled to room temperature and quenched slowly with 2 M aq. HCl. The solution was diluted with ethyl acetate, and the organic portion was washed with 2N aq. HCl, water, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel) eluting with 7% ethyl acetate/hexane) to afford product.

Workup

  1. customTo a dried three-neck round bottom flask fitted with a condenser and addition funnel
  2. additionAfter the addition
  3. temperatureto cool to room temperature
  4. customThe resulting reaction mixture
  5. temperatureThe reaction was cooled to room temperature
  6. customquenched slowly with 2 M aq. HCl
  7. additionThe solution was diluted with ethyl acetate
  8. washthe organic portion was washed with 2N aq. HCl, water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude product was purified by flash chromatography (silica gel)
  13. washeluting with 7% ethyl acetate/hexane)
  14. customto afford product

Sources & evidence

ORD record
ord-d7ad367bdeae402c8105d022d4b80116
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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