Water → 2-Fluoro-6-methoxybenzonitrile

HRID 1983981Notes

Reaction equation

HRID 1983981 reaction equation
F[C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:11][O-:12].[Na+].O>CO>[F:10][C:3]1[CH:2]=[CH:9][CH:8]=[C:7]([O:12][CH3:11])[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 889352,3-DifluorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 5231012-Fluoro-6-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

640.5 g (4.6 mol) of difluorobenzonitrile were dissolved in 3.5 l of methanol and then cooled to 0-5° C. 828.8 g of 30% strength sodium methoxide solution were added dropwise in this temperature range, and the reaction mixture was stirred at room temperature overnight. Then the reaction mixture was added to 20 l of water and the precipitate was filtered off with suction and washed twice with water and twice with heptane. The solid was dried in vacuo at 50° C. Yield: 740 g (99% of theory) of a white solid with a purity of >95% according to GC. 1H NMR (in CDCl3): δ=3.95 ppm (s, 3H, O—CH3), 6.85 ppm (m, 2H, arom. H), 7.5 ppm (q, 1H, arom. H).

Workup

  1. filtrationthe precipitate was filtered off with suction
  2. washwashed twice with water and twice with heptane
  3. customThe solid was dried in vacuo at 50° C

Sources & evidence

ORD record
ord-6d128bc6874749699127c2415ec39c5b
Source dataset
uspto-grants-2009_06
Patent number
US07544637B2

Reaction notes

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