Diethyl Ether → HCID 61078770, compound

HRID 916961Notes

Reaction equation

HRID 916961 reaction equation
[Mg].[F: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]([F:2])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 680214-Fluorobenzyl bromideHCID 810502,4-DichlorobenzonitrileHCID 5462224Magnesium

Product 1

HCID 61078770HCID 61078770, compound

Conditions

Temperature
40 °C

Procedure

To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel flushed with N2 was added magnesium (4.23 g; 174 mmol) and anhydrous ether (100 mL). A solution of 4-flourobenzyl bromide (8.69 mL; 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 into another dried flask charged with a solution of 2,4-dichlorobenzonitrile (10.0 g; 58.0 mmol) in ether (150 mL) under an N2 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, then 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=283 (M+1).

Workup

  1. customTo an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel
  2. customflushed with N2
  3. additionAfter the addition
  4. temperatureto cool to room temperature
  5. customwas cannulated into another dried flask
  6. customThe resulting reaction mixture
  7. temperatureThe reaction was cooled to room temperature
  8. customquenched slowly with 2N aq. HCl
  9. custompartitioned between ethyl acetate and 2N aq. HCl
  10. washThe organic portion was washed with 2N aq. HCl, water, brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. filtrationThe crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane)
  15. customrecrystallized from hexane
  16. customto afford product

Sources & evidence

ORD record
ord-aa5e16d4c7bc4ef0b52c73a9630a880b
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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