Methanol → HCID 86682803, compound

HRID 1504329Notes

Reaction equation

HRID 1504329 reaction equation
[Br:1][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][C:5]([CH2:13][OH:14])=[C:4]([Cl:15])[CH:3]=1.CC(OO)(C)C.[I-].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].[CH3:31][OH:32]>>[CH3:31][O:32][C:13](=[O:14])[C:5]1[CH:6]=[C:7]([O:8][C:9]([F:10])([F:11])[F:12])[C:2]([Br:1])=[CH:3][C:4]=1[Cl:15]

Participants

6

Reactant 5

HCID 887MethanolHCID 4875Potassium IodideHCID 6410tert-Butyl hydroperoxideHCID 24477Sodium ThiosulfateHCID 86682804HCID 86682804, compound

Product 1

HCID 86682803HCID 86682803, compoundYield 39%

Procedure

To a solution of (4-bromo-2-chloro-5-trifluoromethoxy-phenyl)-methanol (6.6 g, 21.61 mmol) in methanol (70 mL) was added 2-methyl-prop-2-yl-hydroperoxide (14.4 mL, 86.42 mmol), and potassium iodide (0.72 g, 4.32 mmol), The reaction mixture was stirred under reflux for 48 h and sat. sodium thiosulfate (20 mL) was added. The reaction mixture was concentrated and extracted with EtOAc (3×100 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, concentrated, and purified by HPLC to provide the title intermediate (2.86 g, 39% yield). (m/z): [M+H]+ calcd for C9H5BrClF3O3 332.91; 334.91. found 332.9; 334.9. 1H NMR (400 MHz, CDCl3): δ(ppm) 7.79 (s, 1H), 7.77 (s, 1H), 3.94 (s, 3H).

Workup

  1. temperatureunder reflux for 48 h
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with EtOAc (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-02376eb44a31496ab295750ac3661345
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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