Dimethylformamide → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

HRID 1267887Notes

Reaction equation

HRID 1267887 reaction equation
[CH:1]1([O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=2I)[CH2:3][CH2:2]1.C([Li])(C)(C)C.CN([CH:25]=[O:26])C.[Cl-].[NH4+]>O1CCCC1>[CH:1]1([O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=2[CH:25]=[O:26])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 117596921-(Cyclopropyloxy)-2-iodo-4-(trifluoromethoxy)benzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 215840762-Cyclopropoxy-5-(trifluoromethoxy)benzaldehydeYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-(Cyclopropoxy)-2-iodo-4-(trifluoromethoxy)benzene (Description 12; 5.84 g, 17 mmol) was dissolved in tetrahydrofuran (150 mL) and cooled to −78° C. Tert-butyl lithium solution (20 mL, 1.7M in pentanes, 34 mmol) was then added dropwise. The solution was stirred at −78° C. for 10 minutes, before N,N′-dimethylformamide (5.3 mL, 68 mmol) was added, and the resulting solution allowed to stir to room temperature. Saturated aqueous ammonium chloride solution (50 mL) was then added and the mixture extracted with diethyl ether (2×100 mL). The extracts were dried (MgSO4) and concentrated to yield an oil. Purification of this by silica chromatography gave the title compound as a clear oil (3.94 g, 16 mmol).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with diethyl ether (2×100 mL)
  3. dry with materialThe extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customto yield an oil
  6. customPurification of this by silica chromatography

Sources & evidence

ORD record
ord-e091803d97b447afa0d2ba3f67453193
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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