Azobisisobutyronitrile → 3-(Bromomethyl)-4-nitrobenzoic acid

HRID 925405Notes

Reaction equation

HRID 925405 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[Br:14][N:15]1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[OH:13][N:11]1[C:10]2[C:2](=[CH:3][C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=2)[CH:1]=[N:15]1.[Br:14][CH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 183703-Methyl-4-nitrobenzoic acidHCID 67184N-bromobutanimide

Product 2

HCID 204936713-(Bromomethyl)-4-nitrobenzoic acidYield 142.7%HCID 89749451HCID 89749451, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-methyl-4-nitrobenzoic acid (539 mg, 2.98 mmol) in benzene (20 mL) was heated to reflux in a sealed tube after which N-bromosuccinimide (679 mg, 3.43 mol) and AIBN (49 mg, 0.298 mol) were carefully added in a portion wise manner over 5 min. After 12 h the mixture was cooled to room temperature, and the succinimide was filtered off and washed with benzene (5 mL×3). The solvent was removed under reduced pressure and purified by column chromatography to give the desired product 3-(bromomethyl)-4-nitrobenzoic acid (553 mg, 68% yield) as a viscous yellow oil.

Workup

  1. additionwere carefully added in a portion wise manner over 5 min
  2. filtrationthe succinimide was filtered off
  3. washwashed with benzene (5 mL×3)
  4. customThe solvent was removed under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-9e1ed92bd6514d8d97a90c03ed8557d8
Source dataset
uspto-grants-2016_03
Patent number
US09284299B2

Reaction notes

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