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

HRID 2395932Notes

Reaction equation

HRID 2395932 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 theresulting 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 withwater 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. temperatureby heating
  2. temperatureat reflux for 7 h
  3. customthe organic layer separated
  4. washwashed withwater and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-582d78bbc8bb4282b9d053f30add9fb3
Source dataset
uspto-grants-1996_02
Patent number
US05491126

Reaction notes

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