Potassium Carbonate → 2-(7-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-oxazole

To a solution of 7-bromo-3,3-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid (example 3b) (1.8 g, 6.64 mmol) in dichloromethane (40 mL) was added several drops of DMF followed by a solution of thionyl chloride in dichloromethane (2.0M, 6.64 mL, 13.3 mmol) at 0° C. under argon. After the addition, the mixture was stirred at room temperature for 5 hours. The solvent and excess of thinoyl chloride were removed under reduced pressure. The residue was dissolved in tetramethylene sulfone (10 mL) and potassium carbonate (1.84 g, 13.3 mmol) and 1H-1,2,3-triazole (504 mg, 7.3 mmol) were added under argon and the mixture was heated to 140° C. for 16 hours. The solution was cooled to room temperature, water was added and the mixture was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: EtOAc/5:1) to give 900 mg of 2-(7-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-oxazole (46%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.40 (s, 6H), 4.41 (s, 2H), 7.19 (s, 1H), 7.67 (s, 1H), 7.75 (d, J=0.88 Hz, 1H), 8.01 (d, J=0.88 Hz).

1. additionAfter the addition
2. customThe solvent and excess of thinoyl chloride were removed under reduced pressure
3. dissolutionThe residue was dissolved in tetramethylene sulfone (10 mL)
4. temperaturethe mixture was heated to 140° C. for 16 hours
5. temperatureThe solution was cooled to room temperature
6. extractionthe mixture was extracted with EtOAc
7. washwashed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated under reduced pressure
11. customThe residue was purified by column chromatography on silica gel (hexane: EtOAc/5:1)

ORD record

ord-d3540867a327418d8fe3397cdee46f79

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196108B2