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Sodium Methoxide → 2,4-Dichloro-6-(methoxymethyl)benzonitrile

HRID 1051947
Notes
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Reaction equation

HRID 1051947 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][O-:14].[Na+]>CO.CCOC(C)=O>[Cl:12][C:7]1[CH:8]=[C:9]([Cl:11])[CH:10]=[C:3]([CH2:2][O:14][CH3:13])[C:4]=1[C:5]#[N:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 897049972-(Bromomethyl)-4,6-dichlorobenzonitrile

Product 1

HCID 210220682,4-Dichloro-6-(methoxymethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

To a suspension of 2-(bromomethyl)-4,6-dichlorobenzonitrile (1.04 mmol) (A.2.2.1.) in 2.5 mL MeOH was added a solution of NaOMe (1.27 mmol, 0.5M in MeOH). The reaction mixture was heated to 50° C. for 1 h. The mixture was conc. in vacuo, redissolved in EtOAc and it was then washed twice with an aq. soln. of KHSO4, twice with a sat. aq. NaHCO3 soln. and once with brine. The org. layer was dried over MgSO4 and conc. in vacuo to give the desired product as orange oil.

Workup

  1. washit was then washed twice with an aq. soln
  2. dry with materiallayer was dried over MgSO4 and conc. in vacuo

Sources & evidence

ORD record
ord-45ac1aaa117e4923b8a9f26fa20c01f3
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388197B2

Reaction notes

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