Dimethylformamide → HCID 86673380, compound

HRID 1023333Notes

Reaction equation

HRID 1023333 reaction equation
C1C[O:4][CH2:3]C1.Br[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1.[Li]CCCC.CN(C=O)C>CCCCCC>[F:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([CH:3]=[O:4])=[CH:8][CH:9]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 67327806HCID 67327806, compoundHCID 178418339Butyllithium

Product 1

HCID 86673380HCID 86673380, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a THF (100 mL) solution of 1-bromo-4-[2-(4-fluorophenoxy)ethyl]benzene (3.05 g) was added 1.6 M solution of n-BuLi in n-hexane (6.80 mL) dropwise at −70° C. under an argon atmosphere. After stirring for 30 minutes, DMF (1.20 mL) was slowly added at −70° C. The resultant mixture was stirred and slowly warmed to −40° C. for 3 hours. The reaction mixture was quenched by addition of saturated aqueous NH4Cl, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 1/1) to afford 4-[2-(4-fluorophenoxy)ethyl]benzaldehyde as a light yellow solid (1.63 g).

Workup

  1. customThe reaction mixture was quenched by addition of saturated aqueous NH4Cl
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water, saturated aqueous NaCl
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 1/1)

Sources & evidence

ORD record
ord-807f2b0d201447cc98e883766e17a99d
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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