Dimethylformamide → 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyran

HRID 977626Notes

Reaction equation

HRID 977626 reaction equation
[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]2[CH:15]=[C:16](I)[CH:17]=[CH:18][C:5]=2[O:4]1.[F:22][C:23]([F:31])([F:30])[C:24]([F:29])([F:28])C([O-])=O.[K+].CN(C)C=O>[Cu]I.C1(C)C=CC=CC=1>[F:28][C:24]([F:29])([C:16]1[CH:17]=[CH:18][C:5]2[O:4][C:3]([CH2:20][F:21])([CH2:2][F:1])[CH:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[C:6]=2[CH:15]=1)[C:23]([F:31])([F:30])[F:22]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 218313442,2-bisfluoromethyl-6-iodo-4-(2-pyridyl)-2H-1-benzopyranHCID 23667659Propanoic acid, 2,2,3,3,3-pentafluoro-, potassium salt (1:1)

Product 1

HCID 218313156-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyranYield 79%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
160 °C

Procedure

A mixture of 1.11 g of 2,2-bisfluoromethyl-6-iodo-4-(2-pyridyl)-2H-1-benzopyran, 1.17 g of potassium pentafluoropropionate, 1.18 g of copper (I) iodide, 20 ml of N,N-dimethylformamide and 7.ml of toluene was stirred at 160° C. under nitrogen gas atmosphere with heating for 3 hours while toluene was distilled off. Ether and water were added thereto and the mixture was filtered using Celite. The mother liquor was extracted with ether. The organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 0.86 g of oily 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyran represented by the following formula.

Workup

  1. distillationwas distilled off
  2. additionEther and water were added
  3. filtrationthe mixture was filtered
  4. extractionThe mother liquor was extracted with ether
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe resultant residue was purified

Sources & evidence

ORD record
ord-813ca9c3823c41b1adec47bef8ec25f2
Source dataset
uspto-grants-1997_03
Patent number
US05614633

Reaction notes

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