N-bromobutanimide → 3-Bromomethyl-5-methyl-benzaldehyde

HRID 426172Notes

Reaction equation

HRID 426172 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([CH3:18])[CH:17]=1)[CH2:5][O:6]C(=O)C1C=CC=CC=1.C1C(=O)N([Br:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl.[W]>[Br:26][CH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([CH3:18])[CH:17]=1)[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13146856Benzoic acid 3,5-dimethyl-benzyl ester

Product 1

HCID 591847343-Bromomethyl-5-methyl-benzaldehydeYield 98.7%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of benzoic acid 3,5-dimethyl-benzyl ester (24 g, 0.1M) and NBS (39.16 g, 0.22M) in carbon tetrachloride (200 ml) was refluxed for 3 hr. under a light of 500 W tungsten lamp. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in ether, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give 21 g of crude 3-bromomethyl-5-methyl-benzaldehyde.

Workup

  1. temperaturewas refluxed for 3 hr
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ether
  5. washwashed with aqueous saturated sodium bicarbonate solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4617f54282e44353853d4fc876310e6e
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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