Azobisisobutyronitrile → 2-Bromo-1-(bromomethyl)-5-methoxy-3-methylbenzene

HRID 723156Notes

Reaction equation

HRID 723156 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH3:11].[Br:12]NC(=O)CCC(N)=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][Br:12]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 2359922-Bromo-5-methoxy-1,3-dimethylbenzeneHCID 9834204N-Bromosuccinamide

Product 1

HCID 102664262-Bromo-1-(bromomethyl)-5-methoxy-3-methylbenzeneYield 92%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2-bromo-5-methoxy-1,3-dimethyl-benzene ((Example 192: step a) 1.01 g, 4.70 mmol) in CCl4 (50 mL) was treated with N-bromosuccinamide and AIBN (catalytic amount) and heated to 75° C. 3.5 h. The reaction was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the product 2-bromo-1-bromomethyl-5-methoxy-3-methyl-benzene (1.27 g, 92%) as a pale orange solid. 1H NMR (CDCl3): δ 6.641 (s, 2H), 4.601 (s, 2H), 3.760 (s, 3H), 2.380 (s, 3H).

Workup

  1. custom3.5 h
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5eb158f17150440ca2628ec6cca86abc
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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