Water → 2-Bromo-5-methoxybenzaldehyde

HRID 1967431Notes

Reaction equation

HRID 1967431 reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[Br:11]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:11][C:7]1[CH:6]=[CH:5][C:4]([O:8][CH3:9])=[CH:3][C:2]=1[CH:1]=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 115693-MethoxybenzaldehydeHCID 67184N-bromobutanimide

Product 1

HCID 3444802-Bromo-5-methoxybenzaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of m-anisaldehyde (55.4 g, 0.41 mol) in DMF (400 mL) was added a solution of N-bromosuccinimide (124.0 g, 0.69 mol) dropwise at room temperature. After the addition, the reaction solution was stirred at room temperature for 12 h, then poured into a mixture of ice and water and stirred for 10 min. The precipitate was collected by filtration and dissolved in ethyl acetate. The resulting solution was washed with water (2×) and brine, dried over sodium sulfate and concentrated in vacuo to give Compound 19 (76.4 g, 87%) as an off-white solid: 1H NMR (CDCl3, 500 MHz) δ 10.32 (s, 1H), 7.53 (d, J=8.5 Hz, 1H), 7.42 (d, J=3.5 Hz, 1H), 7.04 (dd, J=9.0, 3.0 Hz, 1H), 3.85 (s, 3H).

Workup

  1. additionAfter the addition
  2. stirringstirred for 10 min
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in ethyl acetate
  5. washThe resulting solution was washed with water (2×) and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9f22bbeeb744c21bc44ba67145bb593
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

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