Phosphorus tribromide → 2-(Bromomethyl)-4-phenyl-1,3-thiazole

Temperature

22 °C

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 (2.5×6 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).

1. additionadded dropwise over 2 min
2. customA heavy white gum was immediately formed
3. customthe bath was removed
4. customThe reaction mixture was quenched with ice (˜10 g)
5. additionpoured into a mixture of ethyl acetate (150 mL) and saturated sodium bicarbonate (50 mL)
6. washThe organic phase was washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe solid residue was chromatographed on silica gel (2.5×6 cm, elution toluene)

ORD record

ord-a5048f5272d64bd48b5e2485edd3a4af

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303065B2