(2-Bromo-4-fluorobenzo[d]thiazol-6-yl)methanol → 2-Bromo-4-fluorobenzo[d]thiazole-6-carbaldehyde

HRID 1452952Notes

Reaction equation

HRID 1452952 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]([F:13])[C:5]=2[N:6]=1>C1COCC1.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]([F:13])[C:5]=2[N:6]=1

Participants

4

Reactant 1

HCID 57527173(2-Bromo-4-fluorobenzo[d]thiazol-6-yl)methanol

Product 1

HCID 575272232-Bromo-4-fluorobenzo[d]thiazole-6-carbaldehydeYield 61%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2-bromo-4-fluorobenzo[d]thiazol-6-yl)methanol (0.269 g, 1.03 mmol) and manganese (IV) oxide (activated, 85%, 1.47 g, 14.4 mmol) in THF (15 mL) was stirred at rt for 16 hr. Solid material was removed by filtration through Celite® 545, and the filtrate was concentrated under vacuum. The residue was diluted with AcOEt, washed with brine, and dried over anhydrous MgSO4. Evaporation of solvent under vacuum gave the title compound (0.136 g, 61% yield) as a white solid.

Workup

  1. customSolid material was removed by filtration through Celite® 545
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. customEvaporation of solvent under vacuum

Sources & evidence

ORD record
ord-5010c84d973641a3844d488e36ecac98
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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