Hexane → 1-Bromo-3,4-diethoxy-2-fluorobenzene

To a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmoL) in acetonitrile (900 mL), a solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmoL) in acetonitrile (1.5 L) was added dropwise under ice cooling and stirred overnight at room temperature. After evaporation of the solvent, ethyl acetate was added to the residue, followed by washing with water. The resultant aqueous layer was re-extracted with ethyl acetate, and the extract was mixed with the previously obtained organic layer. The organic layer was washed with water, saturated saline and water in this order and then dried over anhydrous magnesium sulfate. The resultant solution was concentrated to obtain an oily material. Hexane was added to the oily material, and the crystals deposited were removed by filtration. The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure to give 205.65 g of the captioned compound (yield: 96%).

1. customAfter evaporation of the solvent, ethyl acetate
2. additionwas added to the residue
3. washby washing with water
4. extractionThe resultant aqueous layer was re-extracted with ethyl acetate
5. additionthe extract was mixed with the previously obtained organic layer
6. washThe organic layer was washed with water, saturated saline and water in this order
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationThe resultant solution was concentrated
9. customto obtain an oily material
10. customthe crystals deposited were removed by filtration
11. concentrationThe solution was re-concentrated
12. customto obtain an oily material, which
13. distillationwas distilled under reduced pressure

ORD record

ord-a972cf25f7104117bbb3b81142838035

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658620B2