Lithium Hydroxide → 3-(2-Bromo-thiazol-4-yl)-acrylic acid

HRID 554863Notes

Reaction equation

HRID 554863 reaction equation
C[O:2][C:3](=[O:12])[CH:4]=[CH:5][C:6]1[N:7]=[C:8]([Br:11])[S:9][CH:10]=1.[OH-].[Li+]>O1CCCC1.O>[Br:11][C:8]1[S:9][CH:10]=[C:6]([CH:5]=[CH:4][C:3]([OH:12])=[O:2])[N:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67459847HCID 67459847, compound

Product 1

HCID 674588783-(2-Bromo-thiazol-4-yl)-acrylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-(2-bromo-thiazol-4-yl)-acrylic acid methyl ester (5.9 g, 23.78 mmol) in tetrahydrofuran (48 mL) and add a solution of lithium hydroxide (636 mg, 26.16 mmol) in water (10 mL). Stir the mixture overnight. Extract the mixture with ethyl acetate and wash twice with water. Acidify the aqueous layer with 1N HCl in water until the mixture is at pH 3-4. Filter the resulting white solid, then wash the solid with ethyl acetate, followed by diethyl ether and then water. Dry the white solid to give 5.05 g (91%) of the desired material.

Workup

  1. extractionExtract the mixture with ethyl acetate
  2. washwash twice with water
  3. filtrationFilter the resulting white solid
  4. washwash the solid with ethyl acetate
  5. customDry the white solid

Sources & evidence

ORD record
ord-0b75bd7791a246c08b3d3c0d8087ad7c
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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