Diethyl Ether → HCID 63492680, compound

HRID 916968Notes

Reaction equation

HRID 916968 reaction equation
[Mg].[CH3:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:13]=1[C:14]#N.CC[O:23]CC>>[Cl:11][C:12]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:13]=1[C:14](=[O:23])[CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH3:2])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 7721p-Xylyl bromideHCID 810502,4-DichlorobenzonitrileHCID 5462224Magnesium

Product 1

HCID 63492680HCID 63492680, compound

Conditions

Temperature
40 °C

Procedure

To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel charged flushed with nitrogen was added magnesium (2.82 g; 116 mmol) and anhydrous ether (100 mL). A solution of 4-methylbenzyl bromide (12.91 g; 69.7 mmol) in ether (50 mL) was added dropwise via the addition funnel at room temperature. After the addition, the reaction mixture was heated at 40° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was cannulated to another dried flask charged with a solution of 2,4-dichlorobenzonitrile (10.0 g; 58.0 mmol) in ether (150 mL) under a nitrogen atmosphere. The resulting reaction mixture was stirred at 40° C. for 6 hours. The reaction was cooled to room temperature and quenched slowly with 2N aq. HCl. Partitioned between ethyl acetate and 2N aq. HCl. The organic portion was washed with 2N aq. HCl, water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane), and recrystallized from hexane to afford product: m/e=279 (M+1).

Workup

  1. customTo an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel
  2. additioncharged
  3. customflushed with nitrogen
  4. additionAfter the addition
  5. temperatureto cool to room temperature
  6. customwas cannulated to another dried flask
  7. customThe resulting reaction mixture
  8. temperatureThe reaction was cooled to room temperature
  9. customquenched slowly with 2N aq. HCl
  10. customPartitioned between ethyl acetate and 2N aq. HCl
  11. washThe organic portion was washed with 2N aq. HCl, water, brine
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. filtrationThe crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane)
  16. customrecrystallized from hexane
  17. customto afford product

Sources & evidence

ORD record
ord-409ed06f080944928b66a087ecd60c8d
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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