ChemicalBook CAS DataBase List 3-BROMO-2-ETHOXYPYRIDINE

3-BROMO-2-ETHOXYPYRIDINE synthesis

6synthesis methods

Product Name:3-BROMO-2-ETHOXYPYRIDINE
CAS Number:57883-25-7
Molecular formula:C7H8BrNO
Molecular Weight:202.05

13534-89-9
323 suppliers
$6.00/1g

64-17-5 Synthesis

64-17-5
757 suppliers
$10.00/50g

57883-25-7
107 suppliers
$72.50/250mg

Yield:57883-25-7 85%

Reaction Conditions:

with sodium for 12 h;Reflux;

Steps:

3-Bromo-2-ethoxypyridine (4a); Typical Procedure

General procedure: Na (2.40 g, 105 mmol) was slowly dissolved in anhyd EtOH (100 mL)while stirring. Then, 2,3-dibromopyridine (7.11 g, 30.0 mmol) wasadded and the reaction mixture was refluxed for 12 h. After quenchingwith sat. aq NH4Cl, the product was extracted with EtOAc. Thecombined organic extracts were dried (Na2SO4) and evaporated invacuo. The crude product obtained was purified by flash chromatography(n-pentane:EtOAc 9:1) to give 4a as a yellow liquid; yield: 5.15g (25.5 mmol, 85%).IR (Diamond-ATR, neat): 2978, 1581, 1471, 1444, 1429, 1381, 13511314, 1297, 1251, 1243, 1068, 1035, 1019, 928, 781, 750, 690 cm-1.1H NMR (400 MHz, CDCl3): = 8.07 (dd, J = 4.9, 1.7 Hz, 1 H), 7.79 (dd,J = 7.6, 1.7 Hz, 1 H), 6.74 (dd, J = 7.6, 4.9 Hz, 1 H), 4.43 (q, J = 7.0 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3 H).13C NMR (101?MHz, CDCl 3): = 159.9, 145.6, 141.7, 117.6, 107.3, 63.0,14.7.MS (EI, 70 eV): m/z (%) = 188 (98), 186 (100), 175 (34), 153 (35), 159(19), 157 (19), 147 (57), 145 (59), 78 (37).HRMS (EI): m/z [M - CH3]+ calcd for C6H5BrNO: 185.9555; found:185.9548

References:

Heinz, Benjamin;Djukanovic, Dimitrije;Siemens, Fiona;Idriess, Mohamed;Martin, Benjamin;Knochel, Paul [Synthesis,2021,vol. 54,# 22,p. 5055 - 5063]

36178-05-9 Synthesis