Azobisisobutyronitrile → 3-(Bromomethyl)-2-chlorobenzonitrile

HRID 1481340Notes

Reaction equation

HRID 1481340 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClC1C=CC=CC=1>[Br:18][CH2:10][C:9]1[C:2]([Cl:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 145298902-Chloro-3-methylbenzonitrile

Product 1

HCID 571606383-(Bromomethyl)-2-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-chloro-3-methylbenzonitrile (6.6 mmol) in 25 mL chlorobenzene was heated to 50° C. when NBS (7.9 mmol) was added. The flask was purged with Ar before AIBN (0.66 mmol) was added at once still at 50° C. The reaction mixture was stirred at 80° C. for 2 h. The solvent was evaporated off, the resulting residue was redissolved in Et2O and washed 3 times with 1N HCl solution and brine. It was dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (85/15) gives the desired compound as white solid.

Workup

  1. additionwas added
  2. additionwas added at once still at 50° C
  3. customThe solvent was evaporated off
  4. dissolutionthe resulting residue was redissolved in Et2O
  5. washwashed 3 times with 1N HCl solution and brine
  6. dry with materialIt was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-ef722ff17bcb47d2b2cd0f6e82143ec4
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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