2,2,2-Trifluoroethanol → HCID 15239003, compound

HRID 1195087Notes

Reaction equation

HRID 1195087 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Br:9][C:10]1[CH:11]=[C:12]([CH3:21])[CH:13]=[C:14]2[C:19]=1[N:18]=[C:17](Cl)[CH:16]=[CH:15]2.C(OCC)(=O)C>O1CCCC1.CCCCCC.C(OCC)(=O)C.O>[Br:9][C:10]1[CH:11]=[C:12]([CH3:21])[CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:16]=[CH:15]2

Participants

8

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 152390028-Bromo-2-chloro-6-methylquinoline

Product 1

HCID 15239003HCID 15239003, compoundYield 88.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To 0.8 g of 60% sodium hydride (oil dispersion) stirring in 20 ml of tetrahydrofuran at room temperature, 2.5 ml (34.3 mmol) of 2,2,2-trifluoroethanol was added dropwise. An exotherm occurred and to the resulting solution 1.7 g (6.7 mmol) of 8-bromo-2-chloro-6-methylquinoline was added followed by heating at reflux for 7 h. Ethyl acetate (200 ml) and excess water was added and the organic layer separated and washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromatography (20:1 followed by 10:1 hexane/ethyl acetate) afforded 1.9 g of 8-bromo-6-methyl-2-(2,2,2-trifluoroethoxy)quinoline, m.p. 61°-62° C.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureat reflux for 7 h
  4. customthe organic layer separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customto give an oil

Sources & evidence

ORD record
ord-5d0bbd720fab4b3498ed41938bf6da91
Source dataset
uspto-grants-1992_05
Patent number
US05110347

Reaction notes

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