Pyridine → 2-Bromo-4-(1-bromoethyl)-1,3-thiazole

HRID 1042340Notes

Reaction equation

HRID 1042340 reaction equation
S(Br)([Br:3])=O.[Br:5][C:6]1[S:7][CH:8]=[C:9]([CH:11](O)[CH3:12])[N:10]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[S:7][CH:8]=[C:9]([CH:11]([Br:3])[CH3:12])[N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 668613171-(2-Bromothiazol-4-yl)ethan-1-ol

Product 1

HCID 668607482-Bromo-4-(1-bromoethyl)-1,3-thiazoleYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution thionyl bromide (0.787 g, 3.78 mmol, 1.05 eq.) in 20 ml dry DCM, cooled to 5° C., was added dropwise a solution of 1-(2-bromo-1,3-thiazol-4-yl)ethanol (0.75 g, 3.60 mmol, 1 eq.) and pyridine (0.285 g, 3.60 mmol, 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 of MgSO4 and evaporated to give 2-bromo-4-(1-bromoethyl)-1,3-thiazole (0.9 g, 84% yield) as a yellow viscous oil.

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 of MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-6ae5e7cedafb4a5d9f9efd7e5a21f2fd
Source dataset
uspto-grants-2013_10
Patent number
US08557849B2

Reaction notes

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