Potassium Cyanide → (4-Bromo-2-chlorophenyl)acetonitrile

HRID 1641532Notes

Reaction equation

HRID 1641532 reaction equation
[C-:1]#[N:2].[K+].[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[C:7]([Cl:13])[CH:6]=1>O.CS(C)=O>[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:1]#[N:2])=[C:7]([Cl:13])[CH:6]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 58762522(4-Bromo-2-chlorophenyl)acetonitrileYield 92.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

Potassium cyanide (587 g) was dissolved in a mixed solution of water (1408 mL) and dimethyl sulfoxide (767 g), and a solution of 4-bromo-2-chlorobenzyl bromide (512 g) of Reference Example 13 in dimethylsulfoxide (1663 g) was added dropwise at an inside temperature of 90° C. After stirring at the same temperature for 1 hr, the reaction mixture was poured into water. After partitioning and extraction with ethyl acetate, the organic layer was washed 4 times with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (383 g) as a brown oil.

Workup

  1. customAfter partitioning
  2. extractionextraction with ethyl acetate
  3. washthe organic layer was washed 4 times with 25% brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6e959a6608984eabac55146826aa1c25
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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