Trimethyl orthoformate → HCID 58374354, compound

HRID 79037Notes

Reaction equation

HRID 79037 reaction equation
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([F:13])[C:3]=1C=O.[CH3:14][O:15][CH:16](OC)[O:17][CH3:18]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>[CH3:14][O:15][CH:16]([O:17][CH3:18])[C:3]1[C:2]([F:1])=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:7][C:6]=1[F:13]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 152053892,6-Difluoro-3-nitrobenzaldehyde

Product 1

HCID 58374354HCID 58374354, compoundYield 143.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,6-difluoro-3-nitro-benzaldehyde (9.0 g, 48.1 mmol), p-toluenesulfonic acid monohydrate (183 mg, 0.962 mmol), trimethylorthoformate (3.5 ml, 32.4 mmol) and methanol (200 ml) was heated at reflux for 4 hours. The reaction mixture was allowed to cool to room temperature and then concentrated in vacuo. The resultant residue was dissolved in DCM (250 mL) and washed with a mixture of water (200 mL) and saturated NaHCO3 solution (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to yield the title compound (10.83 g, 97%). 1H NMR (DMSO-d6, 300 MHz): 8.28 (1 H, ddd, J=9.34, 8.48, 5.51 Hz), 7.39 (1 H, td, J=9.34, 1.81 Hz), 5.66 (1 H, s), 3.40 (6 H, s).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resultant residue was dissolved in DCM (250 mL)
  4. washwashed with a mixture of water (200 mL) and saturated NaHCO3 solution (50 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2310e3bfa0604e4eb410b9c11d020118
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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