Acetonitrile → 1-Chloro-3-(methoxymethoxy)-5-(trifluoromethyl)benzene

HRID 405255

Reaction equation

HRID 405255 reaction equation
Cl[CH2:2][O:3][CH3:4].CC#N.[Cl:8][C:9]1[CH:10]=[C:11]([OH:19])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(OCC)C>[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[C:11]([O:19][CH2:2][O:3][CH3:4])[CH:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7864Chloromethyl Methyl EtherHCID 10796Cesium carbonateHCID 38527183-Chloro-5-hydroxybenzotrifluoride

Product 1

HCID 866742861-Chloro-3-(methoxymethoxy)-5-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Neat chloro(methoxy)methane (1.8 mL, 23.8 mmol) was added to a MeCN solution (20 mL) of 3-chloro-5-(trifluoromethyl)phenol (3.6 g, 18.3 mmol) and Cs2CO3 and the resulting mixture was stirred at room temperature. After 5 h the resulting mixture was diluted with diethyl ether, filtered and concentrated. The resulting material was filtered through a short pad of silica gel, followed by concentration to yield 1-chloro-3-(methoxymethoxy)-5-(trifluoromethyl)benzene.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. filtrationThe resulting material was filtered through a short pad of silica gel
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-177aa0b162824e86a5fb13a3dd1817a8
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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