Triethylamine → 2-Fluoro-4-formylbenzonitrile

HRID 1594886Notes

Reaction equation

HRID 1594886 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>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

5

Reactant 2

HCID 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 (as described in Example 9, Step C) (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). The reaction mixture was maintained at a temperature <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).

Workup

  1. temperatureThe reaction mixture was maintained at a temperature <10° C
  2. stirringThe reaction mixture was stirred at 5° C. for 1 hr
  3. additionafter the addition
  4. custompartitioned between CH2Cl2 and H2O
  5. customThe organic layer was separated
  6. washwashed well with H2O, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1c57d40478c0492bab21761ff189551a
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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