Trifluoroacetic acid → HCID 66643825, compound

(3-bromo-2,4-dimethylphenyl)methanol (2.0 g, 9.3 mmol), and thalium(III) trifluoroacetate (7.50 g, 14.0 mmol) were added to a 250 mL flask containing a stir bar. The flask was then placed in a cooling bath at 0° C. To the flask was added TFA (150 mL) slowly. The resulting mixture was then stirred at room temperature overnight. The TFA was removed under reduced pressure at 30° C. and the resulting residue was redissolved in dichloroethane and concentrated twice (2×100 mL). The residue was then pumped under high vacuum for 45 min. To the dried residue was then added palladium dichloride (165 mg, 0.930 mmol), lithium chloride (788 mg, 18.6 mmol), and magnesium chloride (750 mg, 18.6 mmol). The resulting mixture was dissolved in MeOH (160 mL). The mixture was then degassed and purged with CO (3 times). The flask under CO was stirred at room temp for 4 hours; the color of the reaction mixture changed from white to cream then to brownish. The color of the reaction then finally changed from brownish to black up on which time the reaction had gone to completion as evidenced by LC as well as TLC (hexanes/EtOAc=1/0.3) analysis. The reaction mixture was then poured into a 1 L Erlenmeyer flask containing DCM (400 mL) and EtOAc (400 mL). The solution was then passed through a celite plug, and rinsed several times with DCM until all the organic material had passed through. The solution was then concentrated to dryness, re-dissolved in DCM, absorbed into silica gel, and separated over silica column to give 5-bromo-4,6-dimethyl-2-benzofuran-1(3H)-one. LC-MS: M+1=242

1. additioncontaining a stir bar
2. customThe flask was then placed in a cooling bath at 0° C
3. customThe TFA was removed under reduced pressure at 30° C.
4. dissolutionthe resulting residue was redissolved in dichloroethane
5. concentrationconcentrated twice (2×100 mL)
6. waitThe residue was then pumped under high vacuum for 45 min
7. customThe mixture was then degassed
8. custompurged with CO (3 times)
9. stirringThe flask under CO was stirred at room temp for 4 hours
10. customThe color of the reaction
11. additionThe reaction mixture was then poured into a 1 L Erlenmeyer flask
12. washrinsed several times with DCM until all the organic material
13. concentrationThe solution was then concentrated to dryness
14. dissolutionre-dissolved in DCM
15. customabsorbed into silica gel
16. customseparated over silica column

ORD record

ord-163e36575c9f44a4b34386b31a07c075

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673920B2