Methyl 4-Formylbenzoate → 4-(3,3,3-Trifluoropropenyl)benzoic acid

4 Å molecular sieves (7 g; activated powder) were suspended in 8.8 ml of 1.0 m tbaf in thf and stirred overnight at room temperature under nitrogen. To the solution was added methyl 4-formylbenzoate (160 mg; 0.97 mmol) and 2,2,2-trifluoroethyldiphenylphosphine oxide (415 mg; 1.46 mmol) in 10 ml of anhydrous thf. After stirring overnight, the solvents were evaporated to dryness. The residue was dissolved in EtOAc and washed with water and brine. The organic was dried over Na2SO4, filtered and evaporated. The residue was dissolved in 10 ml of thf and 10 ml of 1N NaOH and refluxed for 30 minutes. The mixture was acidified with concentrated HCl and extracted three times with EtOAc. The organic layers were washed with brine and dried over Na2SO4, filtered and evaporated to give the desired product as a brown powder (125 mg; 60%). M/z=217 (m+1).

1. stirringAfter stirring overnight
2. customthe solvents were evaporated to dryness
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with water and brine
5. dry with materialThe organic was dried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. dissolutionThe residue was dissolved in 10 ml of thf and 10 ml of 1N NaOH
9. temperaturerefluxed for 30 minutes
10. extractionextracted three times with EtOAc
11. washThe organic layers were washed with brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. customevaporated

ORD record

ord-1c151288382746429c72b932f2075c46

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576099B2