Sodium Acetate → 3,5-Dichloro-2-cyanobenzyl acetate

HRID 1051937Notes

Reaction equation

HRID 1051937 reaction equation
Br[CH2:2][C:3]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:4]=1[C:5]#[N:6].[CH3:13][C:14]([O-:16])=[O:15].[Na+]>CC(O)=O>[C:14]([O:16][CH2:2][C:3]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:4]=1[C:5]#[N:6])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 897049972-(Bromomethyl)-4,6-dichlorobenzonitrile

Product 1

HCID 897047603,5-Dichloro-2-cyanobenzyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a soln. of 2-(bromomethyl)-4,6-dichlorobenzonitrile (15.1 mmol) in 30 mL AcOH was added NaOAc (75.7 mmol). The suspension was heated to 100° C. for 2 h. The solvent was evaporated off and the residue partitioned between DCM and water. The org. phase was washed with water, dried over MgSO4 and conc. in vacuo. Purification with CC (5-70% EtOAc/Hept) gives the desired compound as white solid.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue partitioned between DCM and water
  3. washphase was washed with water
  4. dry with materialdried over MgSO4 and conc. in vacuo
  5. customPurification with CC (5-70% EtOAc/Hept)

Sources & evidence

ORD record
ord-49248ed03b8441708d7f4efcba372914
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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