Hydrochloric Acid → HCID 57517323, compound

HRID 1629713Notes

Reaction equation

HRID 1629713 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][C:3]=1[CH3:10].[CH:11]([Mg]Br)([CH3:13])[CH3:12].Cl.CC[O:19]CC>C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:19])[CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 38655354-Chloro-3-methylbenzonitrileHCID 178418365HCID 178418365, compound

Product 1

HCID 57517323HCID 57517323, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-chloro-3-methyl-benzonitrile (5 g, 33 mmol) in benzene (100 mL) was slowly added isopropylmagnesium bromide (1 M in THF, 66 mL, 66 mmol) at room temperature. The solution was then heated to reflux for 3 hours. After cooling in an ice bath, the reaction mixture was carefully treated with 6 M HCl (52 mL). It was then heated to reflux for 2 hours with vigorous mechanical stirring. The mixture was allowed to cool to room temperature, diluted with Et2O (100 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude was purified by Kugelrohr distillation (110-130° C./0.1 Torr). Contaminated fractions were further purified by chromatography on silica gel (cyclohexane/EtOAc).

Workup

  1. customat room temperature
  2. temperatureThe solution was then heated
  3. temperatureto reflux for 3 hours
  4. temperatureAfter cooling in an ice bath
  5. temperatureIt was then heated
  6. temperatureto reflux for 2 hours with vigorous mechanical stirring
  7. washwashed with water and brine
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. distillationThe crude was purified by Kugelrohr distillation (110-130° C./0.1 Torr)
  12. customContaminated fractions were further purified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-61db450429bf436f8ef8623850ce6980
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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