Hydrochloric Acid → 2,4-Dinitro-5-fluorophenoxyacetonitrile

HRID 1381635Notes

Reaction equation

HRID 1381635 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[C:22](#[N:25])[CH2:23][OH:24].Cl>C1(C)C=CC=CC=1>[N+:12]([C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([F:8])=[CH:7][C:2]=1[O:24][CH2:23][C:22]#[N:25])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7857HydroxyacetonitrileHCID 8471TriethylamineHCID 675981,5-Difluoro-2,4-dinitrobenzene

Product 1

HCID 140535322,4-Dinitro-5-fluorophenoxyacetonitrileYield 93.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1,5-difluoro-2,4-dinitrobenzene (7.4 g) and triethylamine (4.4 g) in toluene (74 g) kept at room temperature, a mixture of glycolonitrile (3.1 g) and toluene (6.2 g) was dropwise added, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into 5% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and concentrated to give 2,4-dinitro-5-fluorophenoxyacetonitrile (8.2 g; yield, 93.8%). M.P., 112°-113° C. (recrystallized from ethyl acetate-hexane).

Workup

  1. customkept at room temperature
  2. additionwas dropwise added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-edc80849f37743248b6b4b2bd517a956
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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