Potassium Iodide → HCID 70283150, compound

HRID 363460Notes

Reaction equation

HRID 363460 reaction equation
[NH2:1][CH:2]1[C:7]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:17][F:18])([CH2:15][F:16])[CH:3]1[OH:19].Br[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24](OC)=[O:25].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(#N)C>[F:18][CH2:17][C:4]1([CH2:15][F:16])[C@@H:3]([OH:19])[C@H:2]([N:1]2[CH2:21][C:22]3[C:23](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:24]2=[O:25])[C:7]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 21831361HCID 21831361, compound

Product 1

HCID 70283150HCID 70283150, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.25 g of 4-amino-2,2-bisfluoromethyl-3,4-dihydro-6-nitro-2H-1-benzopyran-3-ol, 0.22 g of methyl 2-bromomethylbenzoate, 0.40 g of potassium carbonate, 0.09 g of potassium iodide and 5 ml of acetonitrile was stirred at 75°-85° C. for 6 hours. Water was added thereto and the mixture was extracted with a mixed solvent of ethyl acetate and ether. After the organic layer was washed with 1N hydrochloric acid and dried, the solvent was distilled off. The resultant residue was purified using silica gel column chromatography (developing solution, AcOEt:hexane=1:1) and recrystallized from a mixed solvent of ethyl acetate and hexane to obtain 0.15 g of trans-2,2-bisfluoromethyl-3,4-dihydro-4-(2,3-dihydro-1-oxo-1H-isoindol-2-yl)-6-nitro-2H-1-benzopyran-3-ol represented by the following formula having a melting point of 285°-288° C.

Workup

  1. extractionthe mixture was extracted with a mixed solvent of ethyl acetate and ether
  2. washAfter the organic layer was washed with 1N hydrochloric acid
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe resultant residue was purified
  6. customrecrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-655835c417cd43358380cfc3da4cb7a7
Source dataset
uspto-grants-1999_02
Patent number
US05874446

Reaction notes

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