Potassium Iodide → 8-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one

HRID 2255196Notes

Reaction equation

HRID 2255196 reaction equation
Br[CH2:2][C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[CH:9][C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C-]#N.[K+].[I-].[K+].[Cl-].C([C:36]([NH3+:55])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC>O.C1(C)C=CC=CC=1>[C:36]([CH2:2][C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[CH:9][C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:55]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 197416778-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-oneHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 197416598-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A suspension of 11.2 g of the above prepared 8-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one, 3.2 g of potassium cyanide, 5.7 g of potassium iodide and 1.3 g of aliquot 336 (tricaprylylmethylammonium chloride) in 45 ml of water and 485 ml of toluene was stirred for 25.5 hours at 73° C., cooled, diluted with water and extracted with methylene chloride. The solvents in the organic layer were concentrated in vacuo and the resulting residue chromatographed over silica gel with 3-5% acetone in a 1:1 mixture of methylene chloride and hexane to give 4.6 g of 8-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one. IR 1643 cm-1 ; NMR (CDCl3): δ 4.06 (2, 1H), 6.8 (s, 1H), 7.0-7.85 (m, 6H), 8.2 (m, 1H).

Workup

  1. additionA suspension of 11.2 g of the
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. concentrationThe solvents in the organic layer were concentrated in vacuo
  5. customthe resulting residue chromatographed over silica gel with 3-5% acetone in a 1:1 mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-4658b88204a747dfb10bfedf79c256df
Source dataset
uspto-grants-1993_08
Patent number
US05238954

Reaction notes

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