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

HRID 1481332Notes

Reaction equation

HRID 1481332 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 solution 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 organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc (95/5 to 30/70) gives the desired compound as white solid.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue partitioned between DCM and water
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-f60fc32ce735477489d4915e23c9c01a
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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