1,4-Dioxane → 3-Benzyloxy-4,5-difluoro-phenol

Temperatur

90 °C

To a solution of potassium hydroxide (2246.7 mg, 40.12 mmol) in 1,4-dioxane (5 mL) and Water (5 mL) was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (212.63 mg, 0.5015 mmol). The reaction mixture was degassed with nitrogen and then treated with tris(dibenzylideneacetone)dipalladium-[0](183.54 mg, 0.2006 mmol) and 1-benzyloxy-5-bromo-2,3-difluoro-benzene [CAS: 1035155-54-4](3 g, 10.03 mmol) the reaction was then heated at 90° C. for 16 hours. The reaction was diluted with aq. KOH solution (2M, 150 mL) and EtOAc (150 mL). The aqueous was separated, and acidified to pH 1 with aq. HCl (2M). The organics were then extracted into EtOAc (150 mL). The organics were separated, washed with brine (150 mL), dried over MgSO4, filtered and concentrated in vacuo to give crude 3-benzyloxy-4,5-difluoro-phenol ˜60% pure);

1. customThe reaction mixture was degassed with nitrogen
2. customThe aqueous was separated
3. extractionThe organics were then extracted into EtOAc (150 mL)
4. customThe organics were separated
5. washwashed with brine (150 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-06037ff7514c44ffb229f87e1ab76e41

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09376436B2