Dimethylformamide → 3-Fluoro-5-propoxybenzaldehyde

HRID 20436Notes

Reaction equation

HRID 20436 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH3:16])[CH:10]=[C:9]([F:17])[CH:8]=1.CN(C)[CH:20]=[O:21]>O1CCCC1>[F:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH3:16])[CH:10]=1)[CH:20]=[O:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 685580051-Bromo-3-fluoro-5-propoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 862368003-Fluoro-5-propoxybenzaldehydeYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add n-butyl lithium (13 mL, 1.6M, 20.76 mmol) to 1-bromo-3-fluoro-5-propoxybenzene (4.40 g, 18.88 mmol) in tetrahydrofuran (100 mL) cooled in a dry ice/acetone bath over 45 minutes, maintaining the internal temperature <−70°. Stir 30 minutes and add N,N-dimethylformamide (2.76 g, 37.75 mmol). Stir 30 minutes and remove cold bath. After 1 hour, quench with saturated aqueous ammonium chloride. Wash organic layer with water and saturated aqueous sodium chloride. Dry (sodium sulfate), filter and concentrate to an oil. Purify on 120 g silica gel eluting with 0 to 10% ethyl acetate in hexanes to give 2.26 g (65.7%) of the desired compound as an oil.

Workup

  1. temperaturecooled in a dry ice/acetone bath over 45 minutes
  2. temperaturemaintaining the internal temperature <−70°
  3. stirringStir 30 minutes
  4. customremove cold bath
  5. waitAfter 1 hour
  6. customquench with saturated aqueous ammonium chloride
  7. dry with materialDry (sodium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate to an oil
  10. customPurify on 120 g silica gel eluting with 0 to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e719edc277814da8a2465485310a9819
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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