ChemicalBook CAS DataBase List 2-broMo-5-cyclopropylpyridine

2-broMo-5-cyclopropylpyridine synthesis

5synthesis methods

Product Name:2-broMo-5-cyclopropylpyridine
CAS Number:1142197-14-5
Molecular formula:C8H8BrN
Molecular Weight:198.06

893738-68-6 Synthesis

893738-68-6
90 suppliers
$45.00/10mg

1142197-14-5
51 suppliers
$106.00/100mg

Yield: 76%

Reaction Conditions:

with copper(ll) bromide;isopentyl nitrite at 25; for 24 h;Inert atmosphere;Sandmeyer Reaction;Reagent/catalyst;

Steps:

General procedure for preparation of halogenopyridines 2, 3
General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76%. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 - 1.82 (m, 1H), 1.10 - 0.98 (m, 2H), 0.75 - 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52%), 199 (41.85%).

References:

Striela, Romualdas;Urbelis, Gintaras;Sūdžius, Jurgis;Stončius, Sigitas;Sadzevičienė, Rita;Labanauskas, Linas [Tetrahedron Letters,2017,vol. 58,# 17,p. 1681 - 1683] Location in patent:supporting information

624-28-2 Synthesis