Methyltriphenylphosphonium iodide → 1,3-Dichloro-2,4-difluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

To the suspension of methyl triphenylphosphonium iodide (1.92 g) in tetrahydrofuran (12 ml) was added potassium tert-butoxide (0.53 g) slowly at argon atmosphere below 0° C. on ice/water bath. The reaction mixture turned to yellow and was stirred for 0.5 h. To the mixture was added a solution of 1-(3,5-dichloro-2,4-difluorophenyl)-2,2,2-trifluoroethanone (1.15 g) in tetrahydrofuran (3 ml) dropwise on ice/water bath. After addition, the reaction mixture was warmed to room temperature and stirred over night. The reaction mixture was diluted with pentane and water. The organic phase was separated and washed with water and dried over MgSO4. The crude residue was purified on silica-gel column chromatography (eluent: n-hexane) to give 1,3-dichloro-2,4-difluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (0.80 g).

1. additionAfter addition
2. stirringstirred over night
3. customThe organic phase was separated
4. washwashed with water
5. dry with materialdried over MgSO4
6. customThe crude residue was purified on silica-gel column chromatography (eluent: n-hexane)

ORD record

ord-5d73e2f8892943f4b0ca6701c131977c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206122B2