Water → 2-Fluoro-3-formyl-6-iodobenzonitrile

HRID 239886Notes

Reaction equation

HRID 239886 reaction equation
[Li+].CC([N-]C(C)C)C.[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[C:11]=1[C:12]#[N:13].[CH:19](OC)=[O:20].O>C1COCC1>[F:9][C:10]1[C:17]([CH:19]=[O:20])=[CH:16][CH:15]=[C:14]([I:18])[C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7865Methyl formateHCID 5227222-Fluoro-6-iodobenzonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 860193492-Fluoro-3-formyl-6-iodobenzonitrileYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LDA (24.3 mL, 2.0 M solution in THF) was added dropwise to a stirred solution of 2-fluoro-6-iodobenzonitrile (10.0 g, 40.5 mmol) in THF (200 mL) at −78° C., and the mixture was stirred for 1 h. Methyl formate (5.0 mL, 81.0 mmol) was added via syringe and the resulting mixture was stirred at −78° C. for 30 min then at rt for 1 h. H2O was added and the mixture was extracted with EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with 20-25% EtOAc/hexanes to give the desired product (8.01 g). MS (ESI(+)) m/e 274.9 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 30 min
  2. waitat rt for 1 h
  3. extractionthe mixture was extracted with EtOAc
  4. washThe extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 20-25% EtOAc/hexanes

Sources & evidence

ORD record
ord-e97bda0cd81a4e958ebf2a550cd499fa
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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