Sodium Cyanide → 2-(3-Bromo-5-methoxyphenyl)acetonitrile

HRID 1686433Notes

Reaction equation

HRID 1686433 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10]O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.S(Cl)(Cl)=O.[C-:16]#[N:17].[Na+]>C(Cl)Cl.C(=O)([O-])O.[Na+].CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:16]#[N:17])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

8

Reactant 3

HCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 10608788(3-Bromo-5-methoxyphenyl)methanol

Product 1

HCID 212429652-(3-Bromo-5-methoxyphenyl)acetonitrileYield 80.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The product from step (iii) (5.38 g) was dissolved in dry DCM (50 ml) and dry DMF (2.3 ml) added followed by thionyl chloride (2.17 ml). The reaction mixture was stirred at RT overnight, and then diluted with aqueous sodium hydrogen carbonate, extracted with DCM, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was dissolved in DMF (20 ml), sodium cyanide (1.30 g) was added and stirred at RT overnight. The reaction mixture was diluted with water, extracted with ether, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 1:2 ether/isohexane) to give the subtitle compound (4.50 g).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an oil
  5. stirringstirred at RT overnight
  6. extractionextracted with ether
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography (eluent 1:2 ether/isohexane)

Sources & evidence

ORD record
ord-95d1468c96a141e5879e233777a23d16
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

Loading…