(6-Bromo-1H-indol-2-yl)methanol → 6-Bromo-1H-indole-2-carbaldehyde

HRID 2365416Notes

Reaction equation

HRID 2365416 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][OH:12])[NH:8]2)=[CH:4][CH:3]=1>C1COCC1.O=[Mn]=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:11]=[O:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 13567957(6-Bromo-1H-indol-2-yl)methanol

Product 1

HCID 135679586-Bromo-1H-indole-2-carbaldehydeYield 55.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (6-bromo-1H-indol-2-yl)methanol (696 mg, 3.00 mmol) in THF (25.0 mL) was added MnO2 (3.20 g, 37.0 mmol) at 0° C. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the title compound (371 mg, 55%) as an orange solid: 1H NMR (500 MHz, CDCl3) δ 9.86 (s, 1H), 9.07 (br s, 1H), 7.64 (s, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.29 (dd, J=8.5, 1.5 Hz, 1H), 7.24 (d, J=1.0 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7270086a570848f593367b117e402975
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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