Benzoic acid, 4-(2-propen-1-yloxy)-2-(trifluoromethyl)- synthesis

Yield:1271469-18-1 30%

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;hexane at -78 - 20;

Steps:

94

To a stirred -78°C stirred solution of the title compound of Preparation 93 (1 g, 2.67 mmol) in THF (30 ml), a 2.5 M solution of butyl lithium in hexanes (1.42 ml, 3.55 mmol) was added dropwise. Then, C0₂ was bubbled in the solution for 20 min and the mixture was allowed to slowly reach rt. Solvent was removed and the resulting slurry was portioned between water and ethyl ether. The aquose layer was then acidified with HCI 2 M and a solid precipitated. It was filtered and dried to yield 200 mg (30%) of the title compound.LRMS: m/z 245 (M-1)⁺ Retention time: 6.03 min (method B)

References:

WO2011/35900,2011,A1 Location in patent:Page/Page column 81