1-Bromo-4-iodobenzene → HCID 68485438, compound

A solution of 1-bromo-4-iodobenzene (Aldrich, 4 g, 14.14 mmol), piperidin-3-ol (Aldrich, 1.14 g, 11.31 mmol), copper (I) iodide (0.269 g, 1.41 mmol) and K3PO4 (6.00 g, 28.3 mmol) in N,N-dimethylformamide (50 mL) under N2 were stirred at 100° C. for 48 h. The reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was washed successively with water and brine then dried over anhydrous Na2SO4, filtered through celite and concentrated under reduced pressure. The sample was purified on silica gel column chromatography using a cyclohexane to cyclohexane/ethyl acetate 70:30 as eluant. The appropriate fractions were combined and concentrated in vacuo and the residue was triturated with pentane. The resulting solid was filtered, washed with pentane and dried to give the title compound 1-(4-bromophenyl) piperidin-3-ol as a beige powder. LCMS: (M+H)+=256-258; Rt=2.90 min.

1. additionThe reaction mixture was poured into ice
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed successively with water and brine
4. dry with materialthen dried over anhydrous Na2SO4
5. filtrationfiltered through celite and
6. concentrationconcentrated under reduced pressure
7. customThe sample was purified on silica gel column chromatography
8. concentrationconcentrated in vacuo
9. customthe residue was triturated with pentane
10. filtrationThe resulting solid was filtered
11. washwashed with pentane
12. customdried

ORD record

ord-1e71582b0a5d4402bd53bc2811553dd6

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061998B2