(7-Bromo-2-methyl-benzo[d]oxazol-4-yl)methanol → 7-Bromo-2-methyl-benzo[d]oxazole-4-carbaldehyde

HRID 1505253Notes

Reaction equation

HRID 1505253 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[N:7][C:6]=2[C:5]([CH2:12][OH:13])=[CH:4][CH:3]=1>ClCCl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[O:13])=[C:6]2[C:10]=1[O:9][C:8]([CH3:11])=[N:7]2

Participants

4

Reactant 1

HCID 58497963(7-Bromo-2-methyl-benzo[d]oxazol-4-yl)methanol

Product 1

HCID 584979577-Bromo-2-methyl-benzo[d]oxazole-4-carbaldehydeYield 63.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (7-bromo-2-methyl-benzo[d]oxazol-4-yl)methanol (Example 6.5) (5.16 g) in dichloromethane (300 ml) was added manganese(IV) oxide (59.9 g) and the suspension stirred at ambient temperature for 16 hours. The reaction mixture was filtered through a plug of silica gel and the filtrate concentrated to give 7-bromo-2-methyl-benzo[d]oxazole-4-carbaldehyde (3.23 g). LC-MS: RT=1.83 min, [M+H]+=240.0/242.0, method A.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of silica gel
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-8a24ab132e7249478c20f756f49b9915
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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