2-(Trifluoromethoxy)benzaldehyde → 5-Nitro-2-(trifluoromethoxy)benzaldehyde

HRID 1819398Notes

Reaction equation

HRID 1819398 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[F:9][C:10]([F:21])([F:20])[O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]>[N+](C)([O-])=O>[N+:7]([C:17]1[CH:18]=[CH:19][C:12]([O:11][C:10]([F:9])([F:20])[F:21])=[C:13]([CH:16]=1)[CH:14]=[O:15])([O-:8])=[O:6]

Participants

4

Reactant 2

HCID 27771922-(Trifluoromethoxy)benzaldehydeHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 196967085-Nitro-2-(trifluoromethoxy)benzaldehydeYield 60.8%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Nitronium tetrafluoroborate (14.0 g, 105 mmol) was added to a solution of 2-trifluoromethoxy-benzaldehyde (10.0 g, 52.6 mmol) in nitromethane (30 mL) at room temperature. The mixture was stirred for 2 h and was then quenched with ice water and extracted with ether (100 mL). The organic layer was separated, washed with water, dried over MgSO4 and chromatographed with 5% EtOAc/hexanes to afford 7.52 g of 5-nitro-2-trifluoromethoxy-benzaldehyde (60.8%) as a pale yellow solid.

Workup

  1. customwas then quenched with ice water
  2. extractionextracted with ether (100 mL)
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customchromatographed with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-d0d95e0849034cef864cda047602610f
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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