HCID 69673313, compound → 3-Bromo-5-[(dimethylamino)methyl]benzaldehyde

HRID 1426306Notes

Reaction equation

HRID 1426306 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([CH2:8][N:9]([CH3:11])[CH3:10])[CH:7]=1>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH2:8][N:9]([CH3:11])[CH3:10])[CH:7]=1)[CH:12]=[O:13]

Participants

4

Reactant 1

HCID 69673313HCID 69673313, compound

Product 1

HCID 866664993-Bromo-5-[(dimethylamino)methyl]benzaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

Manganese(IV) oxide (0.71 g, 8.2 mmol) was added to a solution of {3-bromo-5-[(dimethylamino)methyl]phenyl}methanol (0.40 g, 1.6 mmol, from Step B) in toluene (10 mL). The mixture was heated to 105° C. for 2 hours, then was cooled to room temperature and was filtered and concentrated to afford a light yellow oil (0.31 g, 80%). 1H NMR (400 MHz, CDCl3) δ 9.95 (s, 1H), 7.90 (dd, J=1.7 Hz, 1H), 7.82-7.69 (m, 2H), 3.46 (s, 2H), 2.25 (s, 6H). LCMS (M+H)+: 241.9, 243.9.

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationwas filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-43df38f02f58449bab6735c6641683ec
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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