Hydrochloric Acid → 2-Bromothiazole-5-carboxylic acid

HRID 598872Notes

Reaction equation

HRID 598872 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]([O:9]CC)=[O:8])=[CH:5][N:6]=1.CO.[OH-].[Na+].Cl>>[Br:1][C:2]1[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=1

Participants

5

Procedure

To a 25 mL round-bottomed flask at 0° C. was added ethyl 2-bromothiazole-5-carboxylate (0.633 mL, 4.24 mmol) (commercially available from Aldrich), MeOH (4.25 mL, 4.25 mmol), and sodium hydroxide (2.5 M, 1.88 mL, 4.23 mmol). After 3 hours, 3.5 mL 1 N HCl was added and a white precipitate formed. The MeOH was evaporated by rotary evaporation. The white solid was sonicated with water (20 mL) and filtered washing with water (50 mL). The solid material was dried in a vacuum oven at 60° C. to provide the product (0.69 g, 79%) as a white crystalline solid. LCMS (API-ES) m/z (%): 208 (100%, M−H).

Workup

  1. customa white precipitate formed
  2. customThe MeOH was evaporated by rotary evaporation
  3. customThe white solid was sonicated with water (20 mL)
  4. filtrationfiltered
  5. washwashing with water (50 mL)
  6. customThe solid material was dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-6e0e419c73254e8caac7edb7511d1e5f
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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