2-Fluoro-4-formylbenzonitrile → HCID 21706154, compound

HRID 1594897Notes

Reaction equation

HRID 1594897 reaction equation
[CH2:1]([C:4]1[C:9](Br)=[CH:8][N:7]=[CH:6][C:5]=1[Br:11])[CH:2]=[CH2:3].[Li]CCCC.[F:17][C:18]1[CH:25]=[C:24]([CH:26]=[O:27])[CH:23]=[CH:22][C:19]=1[C:20]#[N:21]>C1COCC1>[CH2:1]([C:4]1[C:5]([Br:11])=[CH:6][N:7]=[CH:8][C:9]=1[CH:26]([OH:27])[C:24]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([F:17])[CH:25]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 112173392-Fluoro-4-formylbenzonitrileHCID 15322740HCID 15322740, compoundHCID 178418339Butyllithium

Product 1

HCID 21706154HCID 21706154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-allyl-3,5-dibromo-pyridine (as described above in Step A) (2.35 g, 8.48 mmol) in THF (100 mL) at −100° C. was added n-BuLi (8.48 mmol), and the mixture was stirred for 5 min. 2-Fluoro-4-formyl-benzonitrile (as described in Example 17, Step A) (1.39 g, 9.33 mmol) in THF (5 mL) was added dropwise via syringe. The reaction mixture was stirred at −78° C. for 1 hr, quenched with saturated NH4Cl (50 mL), and partitioned between EtOAc and saturated NaHCO3. The organic layer was washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound which was purified by chromatography on silica gel with hexane: ethyl acetate 7:3-5:5.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 1 hr
  2. customquenched with saturated NH4Cl (50 mL)
  3. custompartitioned between EtOAc and saturated NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-c3d6f4dee93a451784b5b91f043bbee8
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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