Triphenylphosphine → 4-(Bromomethyl)-2-phenylthiazole

Temperatur

-6 °C

Bromine (177 mg, 1.1 mmol) was added directly into a solution of triphenylphosphine (288 mg, 1.1 mmol) in DCM (2 mL) to give a kind of white precipitate. The temperature was cooled to −6° C. A solution of commercially available (2-phenylthiazol-4-yl)methanol (200 mg, 1.04 mmol) in DCM (1 mL) was added dropwise. The resulting mixture was maintained at −6° C. for 15 min and then warmed to room temperature for 1 h. A white precipitate was formed. The solution was filtered and the white precipitate was washed with DCM. The white precipitate was collected and dissolved in NaHCO3 0.5M After 30 min of stirring, the aqueous layer was extracted with DCM and the organic phase was washed with water, dried over MgSO4, filtered and evaporated to afford 248 mg of 4-(bromomethyl)-2-phenylthiazole (Yield: 71%) as a yellow oil.

1. customto give a kind of white precipitate
2. temperatureThe resulting mixture was maintained at −6° C. for 15 min
3. temperaturewarmed to room temperature for 1 h
4. customA white precipitate was formed
5. filtrationThe solution was filtered
6. washthe white precipitate was washed with DCM
7. customThe white precipitate was collected
8. dissolutiondissolved in NaHCO3 0.5M After 30 min
9. extractionthe aqueous layer was extracted with DCM
10. washthe organic phase was washed with water
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customevaporated

ORD-Eintrag

ord-0a799c9dc1084987af96466ffa2117f7

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08101637B2