ChemicalBook CAS DataBase List 2-(bromomethyl)-4-phenylthiazole

2-(bromomethyl)-4-phenylthiazole synthesis

8synthesis methods

Product Name:2-(bromomethyl)-4-phenylthiazole
CAS Number:78502-79-1
Molecular formula:C10H8BrNS
Molecular Weight:254.15

65384-99-8 Synthesis

65384-99-8
23 suppliers
$75.00/100mg

78502-79-1
54 suppliers
$90.00/250mg

Yield:78502-79-1 80%

Reaction Conditions:

with phosphorus tribromide in dichloromethane at 0 - 22; for 4.2 h;

Steps:

4D 2-(Bromomethyl)-4-phenylthiazole

A solution of (4-phenylthiazol-2-yl)methanol (Example 4C, 0.530 g, 2.77 mmol) in dichloromethane (10 mL) was cooled to 0 °C (ice bath) and treated with PBr₃ (0.118 mL, 1.247 mmol) added dropwise over 2 min. A heavy white gum was immediately formed. After 10 min, the bath was removed and the solution was stirred at 22 °C for 4 h. The reaction mixture was quenched with ice (~10 g) and poured into a mixture of ethyl acetate (150 mL) and saturated sodium bicarbonate (50 mL). The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The solid residue was chromatographed on silica gel (2.5 x 6 cm, elution toluene) to give the title material (0.561 g, 80%>) as a light yellow oil which solidified in the fridge to a pale yellow solid. LC (Method C): 2.062 min. HRMS(ESI) calcd for C₁₀H₉BrNS [M+H]⁺ m/z 253.9634, found 253.9655. ¹H NMR (CDCl₃, 400 MHz) δ ppm: 4.81 (s, 2H), 7.34 - 7.39 (m, 1H), 7.41 - 7.47 (m, 2H), 7.52 (s, 1H), 7.86 - 7.92 (m, 2H).

References:

WO2013/163279,2013,A1 Location in patent:Paragraph 00150