Tetrabutylammonium Fluoride → 2-Chloro-4-((E)-3,3,3-trifluoroprop-1-enyl)benzoic acid

4 Å molecular sieves (powder, 16 g) was added to a 1 M solution of TBAF in THF (20 mL, 20 mmol), and the mixture was stirred at room-temperature overnight under an argon atmosphere. To the mixture were added a solution of methyl 2-chloro-4-formylbenzoate (210 mg, 0.0010 mol) and 2,2,2-trifluoroethyldiphenylphosphine oxide (600 mg, 0.0021 mol) in THF (15 mL). After the mixture was stirred for 2 h, the molecular sieves were removed by filtration. The filtrate was concentrated and water (120 mL) was added. The mixture was extracted with AcOEt. The organic extract was washed with brine, dried (Na2SO4), and concentrated. The residue was chromatographed on silica gel with AcOEt [1% HOAc]-hexane to give the product as a white solid. LC-MS: t=3.12 min, m/z=248.9 & 250.9 (M−1).

1. stirringAfter the mixture was stirred for 2 h
2. customthe molecular sieves were removed by filtration
3. concentrationThe filtrate was concentrated
4. additionwater (120 mL) was added
5. extractionThe mixture was extracted with AcOEt
6. extractionThe organic extract
7. washwas washed with brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. customThe residue was chromatographed on silica gel with AcOEt [1% HOAc]-hexane

ORD record

ord-2280e3d238944ce9bf888665e835056a

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576099B2