Pyridine → 2-Fluoro-4-formylbenzonitrile

HRID 1060877Notes

Reaction equation

HRID 1060877 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 112173392-Fluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-4-hydroxymethylbenzonitrile (10 g, 0,066 mol) and triethylamine (32.3 mL, 0.231 mol) were dissolved in CH2Cl2 (100 mL)—DMSO (20 mL) at <5° C. with stirring and treated dropwise with a solution of pyridine.SO3 complex (31.5 g, 0.198 mol) in DMSO (70 mL) maintaining the reaction mixture temperature at <10° C. The reaction mixture was stirred at 5° C. for 1 hr after the addition, then at 20° C. for 1 hr, then partitioned between CH2Cl2 and H2O. The organic layer was separated, washed well with H2O, brine, and dried (Na2SO4). Filtration and concentration gave the title compound after purification by chromatography (silica gel, hexane: EtOAc, 3:1). 1H NMR (CDCl3) δ 10.06 (d, 1H, J=2 Hz), 7.86 (dd, 1H, J=5,8 Hz), 7.798 (dd, 1H, J=1, 8 Hz), 7.728 (dd, 1H, J=1, 8 Hz).

Workup

  1. stirringThe reaction mixture was stirred at 5° C. for 1 hr
  2. additionafter the addition
  3. custompartitioned between CH2Cl2 and H2O
  4. customThe organic layer was separated
  5. washwashed well with H2O, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-afa462f428fe40c2be28f8609b89d42f
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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