Potassium Fluoride → HCID 86719507, compound

HRID 1772271Notes

Reaction equation

HRID 1772271 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[F-:17].[K+].[F:19][C:20]([F:28])(S(F)(=O)=O)C([O-])=O>CN(C)C=O.[Cu]I>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][C:3]([N+:14]([O-:16])=[O:15])=[C:2]2[C:20]([F:28])([F:17])[F:19])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 22257122HCID 22257122, compoundHCID 86719508HCID 86719508, compound

Product 1

HCID 86719507HCID 86719507, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 1-iodo-7-methoxy-2-nitronaphthalene (3.7 g, 11.24 mmol), CuI (2.3 g, 12.08 mmol) and KF (1 g, 17.24 mmol) in N,N-dimethylformamide (50 ml) was stirred for 0.5 h at 120° C. before the addition of 2,2-difluoro-2-(fluorosulfonyl)acetate (2.3 g, 11.97 mmol). The resulting solution was stirred for another 0.5 h at 120° C. and then quenched by water (300 ml). The crude product was extracted with dichloromethane (3×100 ml) and the organic fractions were combined and washed by brine (3×150 ml). The organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1%-10% ethyl acetate in petroleum ether to afford 7-methoxy-2-nitro-1-(trifluoromethyl)naphthalene as a off-white solid (2 g, 66%). 1H NMR (300 MHz, DMSO): δ 8.48 (d, J=8.7 Hz, 1H), 8.21 (d, J=9.3 Hz, 1H), 7.84 (d, J=8.7 Hz, 1H), 7.56 (dd, J=9.0, 2.1 Hz, 1H), 7.41 (s, 1H), 3.96 (s, 3H).

Workup

  1. customquenched by water (300 ml)
  2. extractionThe crude product was extracted with dichloromethane (3×100 ml)
  3. washwashed by brine (3×150 ml)
  4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give a residue, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9be9bb967d7f44169ae5b5022bc5c814
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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