Trifluoroacetic acid → HCID 66643995, compound

HRID 1474335Notes

Reaction equation

HRID 1474335 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Li+].[Cl-].FC(F)(F)[C:16](O)=[O:17]>Cl[Pd]Cl>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]2[C:5](=[C:6]([F:8])[CH:7]=1)[C:16](=[O:17])[O:10][CH2:9]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 433294Lithium ChlorideHCID 66643901HCID 66643901, compound

Product 1

HCID 66643995HCID 66643995, compound

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

To a solution of (3-bromo-5-fluoro-2-methyl-phenyl)-methanol (1.7 g, 7.76 mmol) in trifluoroacetic acid (20 mL) was added Tl(CF3COO)3 (4.2 g, 7.76 mmol). The resulting mixture was stirred at room temperature overnight, then concentrated to dryness. The residue was dissolved in MeOH (50 mL). To the mixture was added PdCl2 (137 mg, 0.776 mmol), LiCl (652 mg, 15.5 mmol) and MgO (652 mg, 15.5 mmol). The resulting mixture was reacted under a CO (50 psi) atmosphere at room temperature overnight, and then filtered. The filtrate was concentrated and the residue was purified by column chromatography to give 5-bromo-7-fluoro-4-methyl-3H-isobenzofuran-1-one.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in MeOH (50 mL)
  3. customThe resulting mixture was reacted under a CO (50 psi) atmosphere at room temperature overnight
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-505a7cd9daca4ae29e3299dc9bafa661
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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