2,4-Dibromo-1,3-thiazole-5-carbaldehyde → 2,4-Dibromothiazole-5-methanol

HRID 1035014Notes

Reaction equation

HRID 1035014 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([Br:7])[N:6]=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 36928392,4-Dibromo-1,3-thiazole-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 100618132,4-Dibromothiazole-5-methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dibromo-thiazole-5-carbaldehyde (2.0 g, 7.4 mmol) in methanol (80 mL) was treated with NaBH4 (419 mg, 11.0 mmol). The reaction mixture was stirred at rt overnight, quenched with 10% NaOH, diluted with water and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographed using hexane/ethyl acetate (3:1) to give the title compound (1.84 g, 91%). MS (DCI/NH3) m/z 274 (M)+. 1HNMR (500 MHz, CDCl3) δ ppm 2.11 (s, 1 H) 4.78 (s, 2 H).

Workup

  1. customquenched with 10% NaOH
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (2×)
  4. customThe solvent was removed
  5. customthe resulting residue was chromatographed

Sources & evidence

ORD record
ord-0b877e84c8804437af540b5dd5c0f34c
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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