Sodium Methoxide → 2-Methoxy-5-(trifluoromethyl)benzonitrile

HRID 1288268Notes

Reaction equation

HRID 1288268 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][O-:15].[Na+]>>[CH3:14][O:15][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 122239802-Bromo-5-(trifluoromethyl)benzonitrile

Product 1

HCID 177508082-Methoxy-5-(trifluoromethyl)benzonitrileYield 53.7%

Procedure

2-Bromo-5-trifluoromethylbenzonitrile (2.5 g.; prepared as described by M. Gordon, I. J. Pachter and J. W. Wilson, Arzneimittel-Forsch., 1963, 13, 802) and a solution of sodium methoxide (prepared from 0.5 g. sodium and 20 ml. anhydrous methanol) were stirred and refluxed together for 4 hours, and allowed to stand at room temperature overnight. The methanol was evaporated and the residue was acidified with 2N hydrochloric acid, with cooling. The mixture was extracted with diethyl ether, and the extract was dried over anhydrous sodium sulphate, filtered and the filtrate was evaporated, and the residue was recrystallised from pentane to give 2-methoxy-5-trifluoromethylbenzonitrile (1.0g.), m.p. 31°-33° C.

Workup

  1. temperaturerefluxed together for 4 hours
  2. customThe methanol was evaporated
  3. temperaturewith cooling
  4. extractionThe mixture was extracted with diethyl ether
  5. dry with materialthe extract was dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customthe residue was recrystallised from pentane

Sources & evidence

ORD record
ord-98f34e45feb14a259926a2a07c96020b
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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