Benzoyl Peroxide → Methyl 2-(bromomethyl)-4-nitrobenzoate

HRID 1912644Notes

Reaction equation

HRID 1912644 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:15][CH2:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 15088700Methyl 2-methyl-4-nitrobenzoate

Product 1

HCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoateYield 82.4%

Procedure

A degassed solution of methyl 2-methyl-4-nitrobenzoate (3.5 g, 18.19 mmol), N-bromosuccinimide (3.9 g, 21.91 mmol, 1.2 eq) and benzoyl peroxide (3.63 mmol, 0.2 eq.) in 100 ml 0014 was heated at reflux for 4 hr. It was concentrated to dryness, dissolved in ether, washed 2× with water, aq. Na2S2O3, brine, dried over MgSO4, filtered, concentrated and purified by chromatography using 15% ethyl acetate in hexanes to provide 4.11 g of methyl 2-bromomethyl-4-nitrobenzoate.

Workup

  1. temperatureat reflux for 4 hr
  2. concentrationIt was concentrated to dryness
  3. dissolutiondissolved in ether
  4. washwashed 2× with water, aq. Na2S2O3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-918051b00c7d4c8497a86d8a2cc89d33
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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