N-bromobutanimide → Methyl 5-bromo-2-(1-bromoethyl)benzoate

HRID 1749377Notes

Reaction equation

HRID 1749377 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:20][CH3:21])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:20]([Br:1])[CH3:21])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 44226584Methyl 5-bromo-2-ethylbenzoate

Product 1

HCID 90408083Methyl 5-bromo-2-(1-bromoethyl)benzoateYield 104.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

Add N-bromosuccinimide (1090 g, 6.12 mol) and 2,2′-azo-bis-isobutyronitrile (11.4 g, 0.069 mol) to a 20° C. solution of methyl 5-bromo-2-ethylbenzoate (1296 g, 5.33 mol) in carbon tetrachloride (7 L). Heat to reflux for 4 hours, cool to 20-30° C. and wash with water (10 L), extract the aqueous phase with dichloromethane (5 L), combine the organic layers, and wash with water (10 L), Na2SO3 (5 L) and saturated aqueous sodium chloride. Dry with sodium sulfate, filter, and evaporate under reduced pressure to give the title compound as a pale yellow solid (1791 g, 104% crude). ES/MS m/z: 241 (M−HBr).

Workup

  1. temperatureHeat
  2. temperatureto reflux for 4 hours
  3. washwash with water (10 L)
  4. extractionextract the aqueous phase with dichloromethane (5 L)
  5. washwash with water (10 L), Na2SO3 (5 L) and saturated aqueous sodium chloride
  6. dry with materialDry with sodium sulfate
  7. filtrationfilter
  8. customevaporate under reduced pressure

Sources & evidence

ORD record
ord-84c3ff57d35b439f87b4592a1f67064e
Source dataset
uspto-grants-2015_10
Patent number
US09156824B2

Reaction notes

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