Azobisisobutyronitrile → [4-(Bromomethyl)-2-chlorophenyl]methyl acetate

HRID 420756Notes

Reaction equation

HRID 420756 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=1[Cl:13])(=[O:3])[CH3:2].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:33])C(=O)C1>C(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Br:33])=[CH:8][C:7]=1[Cl:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 58001748(2-Chloro-4-methylphenyl)methyl acetate

Product 1

HCID 58001790[4-(Bromomethyl)-2-chlorophenyl]methyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(2-chloro-4-methylphenyl)methyl acetate (453 mg, 2.280 mmol) was dissolved in Chloroform (20 mL) and AIBN (18.72 mg, 0.114 mmol) and NBS (406 mg, 2.280 mmol) were added under Ar atmosphere. The reaction was left under reflux for 5 hours. HPLC showed a new pick which we thought it was the desired product and a bit of starting material and the reaction was stopped. The mixture was allowed to reach room temperature, succinimide was filtered, and volatiles removed under vacuum. Corresponding crude was purified by using flash master chromatography Si II MERCK, 20 g Hexane-acetate (0-30%).

Workup

  1. waitThe reaction was left
  2. temperatureunder reflux for 5 hours

Sources & evidence

ORD record
ord-3c3dd90fecf7432a950ca0cef1ad5d58
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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