Hydrochloric Acid → HCID 22235058, compound

HRID 1743636Notes

Reaction equation

HRID 1743636 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10](#[N:14])[CH2:11][C:12]#[N:13].[BH4-].[Na+].Cl>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][CH:11]([C:10]#[N:14])[C:12]#[N:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 765833-BromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22235058HCID 22235058, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

First, 0.93 g of 3-bromobenzaldehyde and 0.33 g of malononitrile were dissolved in 5 ml of ethanol, to which 1.5 ml of water was added, followed by stirring at room temperature for 4 hours. Then, after cooling at −5° C., a suspension of 57 mg of sodium borohydride in 3 ml of ethanol was added dropwise, followed by stirring at −5° C. for 30 minutes. 10% hydrochloride acid was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.94 g of (3-bromobenzyl)malononitrile (the intermediate (28)).

Workup

  1. additionwas added
  2. temperatureThen, after cooling at −5° C.
  3. additionwas added dropwise
  4. stirringby stirring at −5° C. for 30 minutes
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb06c68198f34eeab680e8689bab8cff
Source dataset
uspto-grants-2006_03
Patent number
US07011838B2

Reaction notes

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