Hydrochloric Acid → 2-((3,5-Dichloro-2-cyanobenzyl)oxy)ethyl acetate

HRID 1481348Notes

Reaction equation

HRID 1481348 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].[C:13]([O:16][CH2:17][CH2:18][OH:19])(=[O:15])[CH3:14].[H-].[Na+].Cl>C1COCC1>[C:13]([O:16][CH2:17][CH2:18][O:19][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])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10960Glycol monoacetateHCID 24758Sodium hydrideHCID 897049972-(Bromomethyl)-4,6-dichlorobenzonitrile

Product 1

HCID 897048262-((3,5-Dichloro-2-cyanobenzyl)oxy)ethyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(bromomethyl)-4,6-dichlorobenzonitrile (1.3 mmol) (A.2.5.1) and 2-hydroxyethyl acetate (1.43 mmol) in 7 mL THF was added NaH (1.95 mmol, 60% suspension in oil). The reaction mixture was stirred at RT overnight and then poured into a 1M HCl solution. The mixture was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (75/25) gives the desired compound as orange oil.

Workup

  1. extractionThe mixture was extracted twice with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-e53df6c0f1f04847b3fac0a09a35f66a
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

Loading…