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

HRID 1051951Notes

Reaction equation

HRID 1051951 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 soln. of 2-(bromomethyl)-4,6-dichlorobenzonitrile (1.3 mmol) (A.2.2.1.) 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 soln. The mixture was extracted twice with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4 and conc. in vacuo. Purification with CC (0-25% EtOAc/Hept) gives the desired compound as orange oil.

Workup

  1. extractionThe mixture was extracted twice with EtOAc
  2. washlayers were washed with brine
  3. dry with materialdried over MgSO4 and conc. in vacuo
  4. customPurification with CC (0-25% EtOAc/Hept)

Sources & evidence

ORD record
ord-d5630ada16484f649a587c07ff98d1b0
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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