Sodium borohydride → 5-Bromo-2-benzothiazoleethanol

HRID 10399

Reaction equation

HRID 10399 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[S:7][C:8]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:9]=2[N:10]=1)C.[BH4-].[Na+]>C1COCC1.CCO>[Br:15][C:12]1[CH:13]=[CH:14][C:8]2[S:7][C:6]([CH2:5][CH2:4][OH:3])=[N:10][C:9]=2[CH:11]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21041508Ethyl 2-(5-bromobenzo[D]thiazol-2-YL)acetate

Product 1

HCID 219800605-Bromo-2-benzothiazoleethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(5-Bromo-benzothiazol-2-yl)-acetic acid ethyl ester (1.25 g, 4.2 mmol) was dissolved in THF (20 mL) and EtOH (5 mL) under N2. Then 0.24 g of NaBH4 was dissolved in EtOH (3 mL) and added to the above solution. The reaction mixture was stirred at room temperature for 2 hours. After the completion the mixture was quenched with water and extracted with CH2Cl2. The aqueous layer was extracted again with more CH2Cl2. The combined methylene chloride layer was dried over anhydrous MgSO4 and filtered. Removal of solvent gave crude product with a yield of 1.11 g. The crude product was used directly in the next step.

Workup

  1. additionadded to the above solution
  2. customAfter the completion the mixture was quenched with water
  3. extractionextracted with CH2Cl2
  4. extractionThe aqueous layer was extracted again with more CH2Cl2
  5. dry with materialThe combined methylene chloride layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customRemoval of solvent
  8. customgave crude product with a yield of 1.11 g

Sources & evidence

ORD record
ord-98cc223bf38a4ce9a090aa143a53649e
Source dataset
uspto-grants-2006_08
Patent number
US07094790B2

Linked notes

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