HCID 86723756, compound → HCID 86723758, compound

HRID 577529Notes

Reaction equation

HRID 577529 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[C:5]([CH3:10])=[C:6]([CH2:8][OH:9])[CH:7]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[C:5]([CH3:10])=[C:6]([CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 86723756HCID 86723756, compound

Product 1

HCID 86723758HCID 86723758, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of [5-bromo-2-methyl-3-(propan-2-yloxy)phenyl]methanol (108a, 25.0 g, 96.5 mmol) in CHCl3 (300 mL) was added MnO2 (42.0 g, 487 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was filtered and the solids were washed with CH2Cl2 (2×20 mL). The filtrate was concentrated under vacuum to give 5-bromo-2-methyl-3-(propan-2-yloxy)benzaldehyde (108b, 18 g, 73%) as a colorless oil.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids were washed with CH2Cl2 (2×20 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-5c6794364cf94751a47eaa7101b1b48e
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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