Azobisisobutyronitrile → 2-(3-(Bromomethyl)-5-methylphenyl)acetic acid

HRID 1255277Notes

Reaction equation

HRID 1255277 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1[CH:11]=[C:12]([CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[C:14]([CH3:16])[CH:15]=1.CC(N=NC(C#N)(C)C)(C#N)C>C(OCC)(=O)C>[Br:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 47494952-(3,5-Dimethylphenyl)acetic acid

Product 1

HCID 581686112-(3-(Bromomethyl)-5-methylphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

NBS (3.12 g) was added portionwise over 1 hour to a solution of 2-(3,5-dimethylphenyl)acetic acid (3.6 g) and AIBN (0.015 g) in ethyl acetate (100 mL) at 50° C. under nitrogen. More AIBN (0.015 g) was added and the mixture was heated to reflux for 3 hours. The reaction mixture was washed with 10% aqueous sodium chloride solution (2×200 mL), dried over magnesium sulphate, filtered and evaporated. The crude material was purified by flash silica chromatography using 20% ethyl acetate in isohexane containing 1% acetic acid as solvent. Fractions containing the product were evaporated to dryness to afford a solid which was triturated with cyclohexane (10 mL) to yield the subtitled compound as a white solid. Yield 2.10 g.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. washThe reaction mixture was washed with 10% aqueous sodium chloride solution (2×200 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash silica chromatography
  8. additionFractions containing the product
  9. customwere evaporated to dryness
  10. customto afford a solid which
  11. customwas triturated with cyclohexane (10 mL)

Sources & evidence

ORD record
ord-e11bc0199357458cb0bedd38c89ff3e0
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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