3-Fluorobenzaldehyde → HCID 57597517, compound

HRID 1158264Notes

Reaction equation

HRID 1158264 reaction equation
[Cl:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=1.[Li]CCCC.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18]>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]([CH:17]([C:4]2[N:3]([CH3:7])[C:2]([Cl:1])=[N:6][CH:5]=2)[OH:18])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 680093-FluorobenzaldehydeHCID 27733322-Chloro-1-methyl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 57597517HCID 57597517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel is added 2-chloro-1-methyl-1H-imidazole (1 equiv.) and THF (0.5 M). The reaction mixture is cooled to −78° C. and n-BuLi (2.5 M in hexanes, 1.05 equiv.) is added. The resulting mixture is stirred for 1 h and a solution of 3-fluorobenzaldehyde (1.05 eq) in THF (2.5 M) is then added dropwise. After the addition is complete, the cooling bath is removed and the reaction is allowed to warm to rt. The reaction mixture is quenched with satd. aq. NH4Cl, transferred to a separatory funnel, and extracted with EtOAc. The organic layer is washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents are evaporated under reduced pressure to yield the product. The material is purified by recrystallization or column chromatography.

Workup

  1. additionAfter the addition
  2. customthe cooling bath is removed
  3. temperatureto warm to rt
  4. customThe reaction mixture is quenched with satd
  5. customaq. NH4Cl, transferred to a separatory funnel
  6. extractionextracted with EtOAc
  7. washThe organic layer is washed with water, brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationAfter filtration
  10. customthe solvents are evaporated under reduced pressure
  11. customto yield the product
  12. customThe material is purified by recrystallization or column chromatography

Sources & evidence

ORD record
ord-ee7e9b64f7734b67b9e3e7b2f1da3205
Source dataset
uspto-grants-2010_10
Patent number
US07807837B2

Reaction notes

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