Sodium borohydride → 2,4-Dibromothiazole-5-methanol

HRID 51547Notes

Reaction equation

HRID 51547 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([Br:7])[N:6]=1.BrC1SC(CO)=C(Br)N=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[S:3][C:4]([CH2:8][OH:9])=[C:5]([Br:7])[N:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22736422(2,4-Dibromo-1,3-thiazol-5-yl)methanol 2,4-Dibromo-1,3-thiazole-5-carbaldehyde

Product 1

HCID 100618132,4-Dibromothiazole-5-methanolYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2,4-Dibromo-1,3-thiazol-5-yl)methanol 2,4-Dibromo-1,3-thiazole-5-carbaldehyde (1.74 g, 6.42 mmol) was dissolved in methanol (70 ml) at 0° C. Sodium borohydride (0.244 g, 6.42 mmol) was added in small portions. The ice-water bath was removed 10 minutes later and the reaction mixture was stirred at room temperature overnight. Solvent was removed and saturated ammonium chloride was added. 1.0N NaOH was added to adjust the pH to 10. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by flash column chromatogrphy to give (2,4-dibromo-1,3-thiazol-5-yl)methanol (0.946 g, 3.47 mmol). 1H NMR (CDCl3-d) δ 2.11 (bs, 1H), 4.79(S, 2H).

Workup

  1. customThe ice-water bath was removed 10 minutes later
  2. customSolvent was removed
  3. additionsaturated ammonium chloride was added
  4. addition1.0N NaOH was added
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash column chromatogrphy

Sources & evidence

ORD record
ord-1764fb67103940bcb5cf17d6c2b90961
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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