Hydrochloric Acid → HCID 66913649, compound

HRID 2104610Notes

Reaction equation

HRID 2104610 reaction equation
[O:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1O)=[CH:15][CH:14]=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=N[C:27]2[C:32](C=1O)=[CH:31][CH:30]=[CH:29][C:28]=2C(F)(F)F.[O-]C1C=CC=CC=1.[K+].Cl>CN(C=O)C.[Cu]>[O:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 23670670Potassium phenoxideHCID 178515289HCID 178515289, compoundHCID 178516855HCID 178516855, compound

Product 1

HCID 66913649HCID 66913649, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

3-phenoxy-8-(trifluoromethyl)quinolin-4-ol: A solution of 3-bromo-8-(trifluoromethyl)quinolin-4-ol (1.28 g, 4.38 mmol), potassium phenoxide (4.24 g, 45.1 mmol), and copper powder (0.100 g, 1.61 mmol) in DMF (30 mL) is treated with CuBr (0.943 g, 6.57 mmol) and heated at reflux for 6 days. The cooled reaction is poured into 2N aq HCl and extracted with ethyl acetate. The combined extracts are washed with sat aq NaHCO3, water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:9 ethyl acetate:hexanes to afford the title compound as a orange solid (0.471, 35%). mp 153-155° C.; Calcd mass for C16H10NF3O2 is 305.25, found by ESI MS, 306 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 days
  3. customThe cooled reaction
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts are washed with sat aq NaHCO3, water, brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe extracts are concentrated
  8. customthe residue is chromatographed with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-8d30db3c08f64faeb2d4f70e63b31217
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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