Nitromethane → HCID 67234079, compound

HRID 216171

Reaction equation

HRID 216171 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:4]=2[O:3]1.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[CH:17][N+:14]([O-:16])=[O:15])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27369732,2-Difluoro-5-formylbenzodioxole2×

Product 1

HCID 67234079HCID 67234079, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,2-difluoro-benzo[1,3]dioxole-5-carbaldehyde [5.48 g, 29.44 mmol, Intermediate (60)] and nitromethane (4.78 mL, 88.32 mmol) in acetic acid (90 mL) is added ammonium acetate (5.67 g, 73.6 mmol). The reaction mixture is heated to reflux for 5.5 hours. Acetic acid is removed in vacuo and the residue is added water (20 mL) and extracted with DCM (3×50 mL), organic layers are combined and washed with 2 N sodium hydroxide, water and brine, dried over sodium sulfate and concentrated. The solid obtained is crystallized in methanol/DCM (1:1) to yield intermediate 2,2-difluoro-5-(2-nitro-vinyl)-benzo[1,3]dioxole [3.83 g, Intermediate (61)] as a solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 5.5 hours
  3. customAcetic acid is removed in vacuo
  4. additionthe residue is added water (20 mL)
  5. extractionextracted with DCM (3×50 mL), organic layers
  6. washwashed with 2 N sodium hydroxide, water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe solid obtained
  10. customis crystallized in methanol/DCM (1:1)

Sources & evidence

ORD record
ord-3e293bf7de3541ec910ea814153fe2fc
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Linked notes

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