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ChemicalBook CAS DataBase List 3-FLUORO-4-(2-FLUOROPHENOXY)ANILINE

3-FLUORO-4-(2-FLUOROPHENOXY)ANILINE synthesis

3synthesis methods
-

Yield:946699-01-0 100%

Reaction Conditions:

with iron;ammonium chloride in water;isopropyl alcohol at 60; for 1 h;

Steps:

6.A EXAMPLE 6 METHYL 3-(6- {6-(2-FLUOROPHENOXY)-5-[4-(METHYLSULFONYL)PHENOXY]- 1H- INDOL-2-YL} PYRIDIN-3 -YL)PROP ANOATE

To a mixture of 2-fluorophenol (10 g, 89 mmol) and 3,4-difluoro-nitro-benzene (14.16 g, 89 mmol) in acetonitrile (100 ml), was added solid K2CO3 (24.60 g, 178 mmol). After heating to 80 °C for lh, the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2S04 and concentrated to afford 2-fluoro-l-(2-fluorophenoxy)- 4-nitrobenzene (8.33 g, 33.2 mmol), which was dissolved in IPA (60 ml) and water (60 ml), mixed with solid NH4C1 (1.774 g, 33.2 mmol) and iron (5.56 g, 99 mmol). The mixture was heated to 60 °C for 1 h, then filtered through a pad of Celite diatomaceous earth. The filter cake was washed with IPA, and filtrate was concentrated to a yellow oil, which was triturated with DCM to remove remaining NH4C1 to give 3-fluoro-4-(2-fluorophenoxy)aniline as an off- white solid (7.34 g, 100% yield).

References:

WO2014/99578,2014,A1 Location in patent:Page/Page column 64