2-Bromo-5-(1,3-dioxan-2-yl)pyridine → 2-Bromo-5-(1,3-dioxolan-2-YL)pyridine

HRID 1401326Notes

Reaction equation

HRID 1401326 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11]C[O:9]2)=[CH:4][N:3]=1>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:9][CH2:11][CH2:12][O:13]2)=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 579672662-Bromo-5-(1,3-dioxan-2-yl)pyridine

Product 1

HCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridineYield 61%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Following the procedure described above for the synthesis of compound 28 (Scheme 8) but substituting 1,3-propanediol (27) for 1,2-ethanediol (34), title compound 35 was obtained in 61% yield [Romero-Salguero, F. J.; Lehn, J-M; Tetrahedron Letters, 40, 1999, 859-862]. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.45 (d, J=2.3 Hz, 1H), 7.79 (ddd, J=8.2, 2.5, 0.4 Hz, 1H), 7.69 (dd, J=8.2, 0.8 Hz, 1H), 5.83 (s, 1H), 4.10-3.93 (m, 4H). MS (m/z): 230.0 (M+H).

Sources & evidence

ORD record
ord-277cf1f5584d42988f1d15946ac98751
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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