1-Bromo-4-iodobenzene → HCID 21072608, compound

HRID 1294669Notes

Reaction equation

HRID 1294669 reaction equation
[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1>>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 115221-Bromo-4-iodobenzeneHCID 15381(+-)-3-Quinuclidinol

Product 1

HCID 21072608HCID 21072608, compound

Procedure

3-Hydroxy quinuclidine (Aldrich, 1.27 g, 10 mmol) was treated with 4-bromo-iodobenzene (Aldrich, 2.82 g, 10 mmol) according to the procedure of Example 14A. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as oil (0.85 g, yield, 30%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.56 (m, 1H), 1.64–1.80 (m, 2H), 1.90–2.08 (m, 1H), 2.10–2.21 (m, 1H), 2.60–3.00 (m, 5H), 3.34–3.40 (m, 1H), 4.46 (m, 1H), 6.83 (d, J=9.5 Hz, 2H) 7.37 (d, J=9.2, Hz, 2H), ppm. MS (DCl/NH3) m/z 282 (M+H)+, 284 (M+H)+.

Workup

  1. customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as oil (0.85 g, yield, 30%)

Sources & evidence

ORD record
ord-d6b38045b9c34c478c88ee43c185994f
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

Loading…