Pyridine → 2-Bromo-4-(bromomethyl)-5-methyl-1,3-thiazole

HRID 1258551Notes

Reaction equation

HRID 1258551 reaction equation
S(Br)([Br:3])=O.[Br:5][C:6]1[S:7][C:8]([CH3:13])=[C:9]([CH2:11]O)[N:10]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[S:7][C:8]([CH3:13])=[C:9]([CH2:11][Br:3])[N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 58127549(2-Bromo-5-methylthiazol-4-yl)methanol

Product 1

HCID 671901442-Bromo-4-(bromomethyl)-5-methyl-1,3-thiazoleYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution thionyl bromide (2.27 g, 10.94 mmol, 1.1 eq.) in 25 ml dry DCM, cooled to 5° C., was added dropwise a solution of (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol (2.07 g, 9.94 mmol, 1 eq.) and pyridine (0.865 g, 10.94 mmol, 1.1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred 1.5 hr. 100 ml of water and 100 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to give 2-bromo-4-(bromomethyl)-5-methyl-1,3-thiazole (1.94 g, 72% yield) as a white solid.

Workup

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition100 ml of water and 100 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d64e7b78604e415bb14d565c873d8b19
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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