3,5-Dibromophenylacetic acid → HCID 19048532, compound

A solution of (3,5-dibromo-phenyl)acetic acid (1.543 g, 5.2 mmol) in tetrahydrofuran (40 mL) was cooled to 0° C. Within 30 minutes borane tetrahydrofuran complex (1 M, 9.19 mL) was added. After complete addition the ice bath was removed and the reaction mixture warmed to room temperature within 25 minutes. After 3 hours, the mixture was cooled to −2° C., quenched by addition of methanol (10 mL) and evaporated under reduced pressure. The residue was dissolved in dichloromethane, the resulting solution was washed with hydrochloric acid (1 N, 50 mL), a saturated solution of sodium hydrogencarbonate (50 mL), and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure and yielded. The residue was chromatographed on silica gel using a gradient of heptane/ethyl acetate=100/0 to 2/1 as the eluent. There were obtained 1.29 g (88% of theory) of the title compound as a light yellow oil.

1. additionWithin 30 minutes borane tetrahydrofuran complex (1 M, 9.19 mL) was added
2. customwas removed
3. temperaturethe mixture was cooled to −2° C.
4. customquenched by addition of methanol (10 mL)
5. customevaporated under reduced pressure
6. dissolutionThe residue was dissolved in dichloromethane
7. washthe resulting solution was washed with hydrochloric acid (1 N, 50 mL)
8. dry with materialThe organic layer was dried over sodium sulfate
9. customevaporated under reduced pressure
10. customyielded
11. customThe residue was chromatographed on silica gel using a gradient of heptane/ethyl acetate=100/0 to 2/1 as the eluent

ORD record

ord-4b5b371649fd46cdb0d66d22094de380

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989449B2