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

HRID 1430384Notes

Reaction equation

HRID 1430384 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-fc59f0c731e64496b6a2b3b593b089de
Source dataset
uspto-grants-2015_01
Patent number
US08940778B2

Reaction notes

Loading…