2-(3-bromophenyl)-2,2-difluoroacetic acid synthesis
- Product Name:2-(3-bromophenyl)-2,2-difluoroacetic acid
- CAS Number:885068-76-8
- Molecular formula:C8H5BrF2O2
- Molecular Weight:251.02
150529-73-0
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885068-76-8
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Yield:885068-76-8 98%
Reaction Conditions:
Stage #1: methyl 2-(3-bromophenyl)acetateewith sodium hexamethyldisilazane in tetrahydrofuran at -78; for 0.416667 h;
Stage #2: with N-fluorobis(benzenesulfon)imide in tetrahydrofuran; for 3.58333 h;
Steps:
28.1
To an anhydrous THF solution (0.5 M) of methyl 2-(3-bromophenyl)acetate (1 eq.) was added, at -78 °C, sodium hexamethyldisilazide (2.2 eq., 1 M THF solution) dropwise over a period of 5 min. The resulting pale yellow solution was stirred at -78 °C for 20 min before N-fluoro-N-(phenylsulfonyl)- benzenesulfonamide (2.2 eq., 0.5 M THF solution) was added dropwise over a period of 10 min. After 3.5 hrs, the reaction mixture was quenched carefully with the dropwise addition of 1 N aq. HC1. The aqueous layer was separated and back- extracted with ether. The combined organic extracts were then washed sequentially with 10% aq. NaHCOs, water and brine. The organic extract was dried over sodium sulfate and filtered. Concentration of the filtrate in vacuo afforded a pale yellow semi-solid. This was then briefly sonicated in 1 :1 (v/v) hexanes and ether. The resulting suspension was then filtered through a bed of celite and the filtrate was concentrated in vacuo to afford methyl 2-(3-bromophenyl)-2,2-difluoroacetate as a yellow oil (98% yield).
References:
WO2013/134562,2013,A1 Location in patent:Paragraph 00170
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