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

HRID 1505242Notes

Reaction equation

HRID 1505242 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 (Example 5.2) (20.22 g) 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-3b53fb16fb384addbdd88e5d3602d48d
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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