Hydrochloric Acid → HCID 86712401, compound

HRID 2174196Notes

Reaction equation

HRID 2174196 reaction equation
[Br:1][C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[C:9]#N)=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl.C(=O)([O-])[OH:25].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:25])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21225700Diisobutylaluminumhydride2×HCID 867123981415018-68-6

Product 1

HCID 86712401HCID 86712401, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.8 g of 2-(3-bromo-pyridin-2-yl)-2-methyl-propionitrile were dissolved in 20 ml of toluene. 5.9 ml of a 25% by weight toluene solution of diisobutylaluminum hydride were added thereto at 0° C. The mixture was stirred for 17 hours at room temperature. Subsequently, dilute hydrochloric acid was added thereto to dissolve the unreacted diisobutylaluminum hydride. Continuing, aqueous saturated sodium hydrogen carbonate solution was added thereto followed by extracting with ethyl acetate. The solvent of the organic phase was distilled off followed by purifying by silica gel column chromatography to obtain 0.44 g of 2-(3-bromo-pyridin-2-yl)-2-methyl-propioaldehyde.

Workup

  1. customat 0° C
  2. extractionby extracting with ethyl acetate
  3. distillationThe solvent of the organic phase was distilled off
  4. customby purifying by silica gel column chromatography

Sources & evidence

ORD record
ord-5726306167bb45db90d7f12dd561f89f
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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