(7-Bromo-benzo[1,2,5]thiadiazol-4-yl)-methanol → 7-Bromo-2,1,3-benzothiadiazole-4-carboxaldehyde

HRID 536418Notes

Reaction equation

HRID 536418 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([CH2:11][OH:12])=[CH:4][CH:3]=1>ClCCl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([CH:11]=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58497958(7-Bromo-benzo[1,2,5]thiadiazol-4-yl)-methanol

Product 1

HCID 584979627-Bromo-2,1,3-benzothiadiazole-4-carboxaldehydeYield 83%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (7-bromo-benzo[1,2,5]thiadiazol-4-yl)-methanol (20.22 g) (Example I2) in dichloromethane (185 ml) was added manganese(IV) oxide (71.7 g). The suspension was stirred at ambient temperature for 16 hours. The reaction mixture was filtered through a plug of Celite®. The filtrate was concentrated to give 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde (16.65 g) as an orange solid. 1H-NMR (400 MHz, CDCl3): 10.74 (s, 1H), 8.11-8.05 (m, 2H) ppm.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite®
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0e8d202a695d4a0b99fb96e48552fe4c
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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