Methanol → 4-Nitro-2-(trifluoromethyl)benzaldehyde

HRID 2424638Notes

Reaction equation

HRID 2424638 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#N)=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)([O-:3])=[O:2].CC(C[AlH]CC(C)C)C.CO.S(=O)(=O)(O)[OH:28]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:28])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14487Diisobutylaluminum hydrideHCID 27757834-Nitro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 123911054-Nitro-2-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4-nitro-2-(trifluoromethyl)benzonitrile (100 mg, 0.463 mmol) in toluene (3 mL) at 0° C. under argon was added DIBAL-H (0.51 mL, 1M in toluene, 0.51 mmol) and the reaction stirred for 3.75 h. MeOH and sulphuric acid were added and the reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was concentrated and the residue was portioned between EtOAc (10 mL) and water (10 mL). The organic phase was dried and concentrated to give the crude product which was purified by column chromatography eluting with 0-15% EtOAc/petroleum ether to give the title compound as a yellow oil (91 mg), δH (CDCl3, 400 MHz) 10.47 (1H, s), 8.66 (1H, d), 8.56 (1H, dd), 8.33 (1H, d).

Workup

  1. stirringstirred for 1 h
  2. concentrationThe mixture was concentrated
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography
  7. washeluting with 0-15% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-aa32162297664512b486e4c0df72d04c
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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