Ethanol → HCID 90422615, compound

HRID 1477749Notes

Reaction equation

HRID 1477749 reaction equation
[H-].[Na+].[CH3:3][CH2:4][OH:5].F[C:7]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10]>CN(C=O)C>[CH2:4]([O:5][C:7]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 889352,3-Difluorobenzonitrile

Product 1

HCID 90422615HCID 90422615, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH 60% dispersion in mineral oil (575 mg, 14.4 mmol) was added to a rt solution of EtOH (1.0 mL, 17.1 mmol) in DMF (6.0 mL). After stirring for 40 min at rt, the solution was cooled to 0° C., 2,3-difluorobenzonitrile (1.59 mL, 14.4 mmol) was added dropwise and stirring was continued for 1 h at rt. The rxn mixture was quenched with water and extracted with DCM (2×). The combined org. layers were dried (MgSO4), filtered and concentrated in vacuo to yield 2-ethoxy-3-fluorobenzonitrile as an orange oil. LC-MS B: tR=0.74 min; [M+H]++=no ionization. 1H NMR (CDCl3) δH: 7.66 (m, 2H), 7.27 (m, 1H), 4.32 (q, 2H), 1.35 (t, 3H).

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. stirringstirring
  3. waitwas continued for 1 h at rt
  4. customThe rxn mixture was quenched with water
  5. extractionextracted with DCM (2×)
  6. dry with materiallayers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-590e8dff23354d12818752a539c05403
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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