Potassium Fluoride → Methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

To a stirred mixture of methyl 3-bromo-5-formylbenzoate (0.60 g, 2.5 mmol), tetra-N-butylammonium bromide (0.90 g, 2.8 mol), potassium fluoride (10 mg, 0.17 mmol), and toluene (10 mL) at −20° C. was added (trifluoromethyl)trimethylsilane (0.74 mL, 5.0 mmol). The reaction mixture was stirred for 20 min, and then quenched with water. To the mixture were added 1 M HCl aqueous solution (2 mL) and 1,4-dioxane (12 mL), and the mixture was stirred for 30 min. The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by flash column to afford the title compound.

1. customquenched with water
2. additionTo the mixture were added 1 M HCl aqueous solution (2 mL) and 1,4-dioxane (12 mL)
3. stirringthe mixture was stirred for 30 min
4. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
5. washThe combined organic layers were washed with brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash column

ORD record

ord-ca17c538327649b4b9f7a8100d598f26

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946439B2