1-Bromo-4-iodobenzene → HCID 71145454, compound

Temperature

-25 °C

To a solution of 1-bromo-4-iodobenzene (1.462 g, 5.17 mmol) in THF (13 ml) at −30° C. to −25° C. was added isopropylmagnesium chloride 2M in THF (2.82 ml, 5.64 mmol). The reaction mixture was stirred at −30 to −20° C. for 2 hrs, allowed to warm to −3° C. and 9-thia-bicyclo[3.3.1]nonane-3-carbaldehyde (800 mg, 4.70 mmol) was added, the syringe was rinsed with THF (1 ml) and the solution was stirred for 1.5 hrs while cooled in an ice bath. The reaction mixture was quenched at 0° C. with a solution of aqueous saturated NH4Cl and water 2/1 (15 ml), diluted with ethyl acetate and extracted with ethyl acetate. The organic phases were combined, washed with brine, dried using Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluting with a gradient of hexanes:MTBE 98:02 to 70:30) yielding the title intermediate (1.11 g, 2.88 mmol, 61%) as a colourless resin.

1. temperatureto warm to −3° C.
2. washthe syringe was rinsed with THF (1 ml)
3. stirringthe solution was stirred for 1.5 hrs
4. temperaturewhile cooled in an ice bath
5. customThe reaction mixture was quenched at 0° C. with a solution of aqueous saturated NH4Cl and water 2/1 (15 ml)
6. additiondiluted with ethyl acetate
7. extractionextracted with ethyl acetate
8. washwashed with brine
9. customdried
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe crude product was purified by silica gel column chromatography (
13. washeluting with a gradient of hexanes:MTBE 98:02 to 70:30)

ORD record

ord-362cfec24fe34d04a9cda17643d8d139

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859535B2