(7-Bromo-2-methyl-benzo[d]oxazol-4-yl)methanol → 7-Bromo-2-methyl-benzo[d]oxazole-4-carbaldehyde
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]2Participants
4
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
- filtrationThe reaction mixture was filtered through a plug of silica gel
- concentrationthe filtrate concentrated
Sources & evidence
- ORD record
- ord-8a24ab132e7249478c20f756f49b9915
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216973B2
Reaction notes
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