Potassium Iodide → HCID 66701230, compound

HRID 2062059Notes

Reaction equation

HRID 2062059 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([F:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:16])=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[F:25][C:26]([F:36])([F:35])[C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([F:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:16][CH2:31][C:30]1[CH:29]=[CH:28][C:27]([C:26]([F:25])([F:35])[F:36])=[CH:34][CH:33]=1)=[O:4]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 516892Sodium BicarbonateHCID 66701165HCID 66701165, compound

Product 1

HCID 66701230HCID 66701230, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.190 g of 4-fluoro-1-hydroxynaphthalene-2-carboxylic acid methyl ester in 4 ml of dry DMF 560 mg of Cesium carbonate and 31 mg of potassium iodide was added. The mixture was stirred at ambient temperature for 20 minutes after which was added a solution of 0.31 g of 4-(trifluoromethyl)benzyl bromide in 2 ml of DMF. The mixture was stirred at room temperature for 3 h, poured into saturated sodium bicarbonate, extracted with ethyl acetate, washed with water, brine, dried (sodium sulphate), filtered and concentrated to a white solid. The material was purified by flash chromatography on silica gel eluting with ethyl acetate/heptanes to provide 0.231 g of 4-fluoro-1-[4-(trifluoromethyl)benzyloxy]naphthalene-2-carboxylic acid methyl ester as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated to a white solid
  7. customThe material was purified by flash chromatography on silica gel eluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-c2d6f2634a434626a02ef592e52f4bb4
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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