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

HRID 274208Notes

Reaction equation

HRID 274208 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-trifluorethanol was added dropwise. An exotherm occurred and to the resulting solution 1.7 g (6.7 mmol) of 8-bromo-2-chloro-6-methyl-quinoline 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-c86d76fa9f244248a5fa18a1f1ec45fd
Source dataset
uspto-grants-1995_02
Patent number
US05389600

Reaction notes

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