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

HRID 536440Notes

Reaction equation

HRID 536440 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 (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, using the following method:

Workup

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

Sources & evidence

ORD record
ord-2138f8ba62d944b3a6c223a6aae3d104
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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