N-bromobutanimide → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

HRID 1694393Notes

Reaction equation

HRID 1694393 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([Cl:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:10])=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27355544-Bromo-2-chlorotoluene

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneYield 65.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4-Bromo-2-chloro-1-methylbenzene (CAS 89794-02-5, 30 g, 0.15 mol) and N-bromosuccinimide (26 g, 0.15 mol) were mixed in CCl4 (300 mL). Azobis(2-methylpropionitrile) (˜0.3 g) was added in portions under vigorous stirring and refluxing. The mixture was refluxed for 30 min and cooled. The precipitate was filtered off and discarded. The filtrate was evaporated. The residue was distilled at 1 mmHg, bp 75° C. to give the title compound (28 g, 65%). 1H NMR data (CDCl3): δ 7.57 (d, J=1.9 Hz, 1H ArH), 7.39 (dd, 1H, J1=1.9 Hz, J2=8.1 Hz, ArH), 7.31 (d, 1H, J=1.9 Hz, ArH), 4.53 (s, 2H, ArCH2).

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was refluxed for 30 min
  3. temperaturecooled
  4. filtrationThe precipitate was filtered off
  5. customThe filtrate was evaporated
  6. distillationThe residue was distilled at 1 mmHg, bp 75° C.

Sources & evidence

ORD record
ord-1e220b7bc3574b1382723effe79f2df7
Source dataset
uspto-grants-2012_04
Patent number
US08158673B2

Reaction notes

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