Trifluoroacetic acid → 5-Bromo-4-methylisobenzofuran-1(3H)-one

To a flask charged with (3-bromo-2-methylphenyl)methanol (6.0 g, 30 mmol) was added a 1M TFA solution of Thallium Trifluoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT overnight. The solvent was removed under vacuum, and the residue was pumped under high vacuum for 30 min to ensure complete removal of TFA. To the residue was then added palladium(II) chloride (529 mg, 2.98 mmol), lithium chloride (2.53 g, 59.7 mmol), magnesium oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at RT. Analysis by LC showed a formation of product within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The solution was filtered through a celite pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to provide the title compound

1. customThe solvent was removed under vacuum
2. waitthe residue was pumped under high vacuum for 30 min
3. customremoval of TFA
4. customThe reaction was flushed with CO twice
5. customkept under CO at RT
6. customwithin 2 hours
7. additionTo this solution was added ethyl acetate
8. customto precipitate the salts
9. filtrationThe solution was filtered through a celite pad
10. washwashed with EtOAc
11. custompurified by silica gel chromatography

ORD record

ord-44c963350aa649c08d4db388c41cdbb7

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999991B2