2,2,2-Trifluoroethanol → HCID 15239024, compound

HRID 2395936Notes

Reaction equation

HRID 2395936 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Br:9][C:10]1[C:15]2[N:16]=[C:17](Cl)[N:18]=[N+:19]([O-:20])[C:14]=2[CH:13]=[C:12]([CH3:22])[CH:11]=1.C(OCC)(=O)C>O1CCCC1.O>[Br:9][C:10]1[C:15]2[N:16]=[C:17]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[N:18]=[N+:19]([O-:20])[C:14]=2[CH:13]=[C:12]([CH3:22])[CH:11]=1

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 15239023HCID 15239023, compound

Product 1

HCID 15239024HCID 15239024, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.5 g of 60% sodium hydride stirring in 30 ml of tetrahydrofuran, 3.0 mlof 2,2,2-trifluoroethanol was added dropwise at ambient temperature. A solution resulted and 2.0 g (7.29 mmol) of the above 5-bromo-3-chloro-7-methyl-1,2,4-benzotriazine-1-oxide was added and at ambient temperature and the mixture stirred 2 h. Ethyl acetate (200 ml) and excess water were added and the separated organic extract washed with water, brine, and dried over magnesium sulfate. The solvent was removed invacuo, hexane added to the residue, and the suspended yellow s 61id filtered and dried to afford 1.7 g of 5-bromo-7-methyl-3-(2,2,2-trifluoroethoxy) -1,2,4-benzotriazine-1-oxide, m.p. 127°-128° C.

Workup

  1. customA solution resulted
  2. extractionthe separated organic extract
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed invacuo, hexane
  6. additionadded to the residue
  7. filtrationthe suspended yellow s 61id filtered
  8. customdried

Sources & evidence

ORD record
ord-e75a51142bd84b76b9a15c863258fa15
Source dataset
uspto-grants-1996_02
Patent number
US05491126

Reaction notes

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