2-Fluoro-5-nitrobenzonitrile → HCID 86704472, compound

HRID 1754419Notes

Reaction equation

HRID 1754419 reaction equation
[OH:1][CH:2]1[CH2:5][O:4][CH2:3]1.CC(C)([O-])C.[K+].F[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]>C1COCC1>[N+:21]([C:18]1[CH:19]=[CH:20][C:13]([O:1][CH:2]2[CH2:5][O:4][CH2:3]2)=[C:14]([CH:17]=1)[C:15]#[N:16])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 5194172-Fluoro-5-nitrobenzonitrileHCID 9942117Oxetan-3-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 86704472HCID 86704472, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Hydroxy oxetane (370 mg, 5 mmol, 2 equiv) in THF (15 ml) under argon gas, was cooled to 0° C. Potassium tert-butoxide (617 mg, 5.5 mmol, 2.2 equiv) was added in one portion, and the reaction mixture was stirred for 20 minutes at 0° C. Then 2-fluoro-5-nitrobenzonitrile (415 mg, 2.5 mmol, 1 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0° C. and allowed to warm up to ambient temperature over 1 hour. The reaction mixture was concentrated, and the residue was taken in DCM and water. The layers were separated, and the organic layer was washed with water (×2), dried over Na2SO4, filtered, and concentrated to provide 5-nitro-2-(oxetan-3-yloxy)benzonitrile (495 mg, 90%) as a brown-yellow solid that was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes at 0° C.
  2. temperatureto warm up to ambient temperature over 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. customThe layers were separated
  5. washthe organic layer was washed with water (×2)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f2733f02c78b48fcb978163d2b5a2d15
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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