Hydrochloric Acid → 2-Bromothiazole-5-carboxylic acid
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]=1Participants
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
- customa white precipitate formed
- customThe MeOH was evaporated by rotary evaporation
- customThe white solid was sonicated with water (20 mL)
- filtrationfiltered
- washwashing with water (50 mL)
- 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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