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

HRID 2039414Notes

Reaction equation

HRID 2039414 reaction equation
[Br:1]N1C(=O)CCC1=O.[I:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[CH3:17]>ClC1C=CC=CC=1.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>[I:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[CH2:17][Br:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 154429474-Bromo-2-iodo-1-methylbenzene

Product 1

HCID 532313074-Bromo-1-(bromomethyl)-2-iodobenzeneYield 24.2%

Reagents, catalysts & solvents 2

HCID 11229634Benzyl PeroxideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

N-Bromosuccinimide (NBS) (1.1 molar equivalents, 66.5 g, 373 mmol) and benzyl peroxide (0.006 molar equivalent, 450.7 mg, 1.9 mmol) are added to a solution of 2-iodo-4-bromotoluene 6 (1 molar equivalent, 100.3 g, 338 mmol) in chlorobenzene (1200 ml). The batch is then stirred under reflux overnight. After the solvent has been removed in a rotary evaporator, ethyl acetate and water are added. The aqueous phase is extracted by shaking with ethyl acetate. The organic phase is washed by shaking with water, dried and evaporated in a rotary evaporator. The product 7 (30.7 g, 24%) is obtained in the form of a white powder by recrystallisation from ethanol (50 ml).

Workup

  1. temperatureunder reflux overnight
  2. customAfter the solvent has been removed in a rotary evaporator, ethyl acetate and water
  3. additionare added
  4. extractionThe aqueous phase is extracted
  5. stirringby shaking with ethyl acetate
  6. washThe organic phase is washed
  7. stirringby shaking with water
  8. customdried
  9. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-c1654333ecc6495ebafb0d1456e354dd
Source dataset
uspto-grants-2013_11
Patent number
US08580395B2

Reaction notes

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