N-bromobutanimide → 3-Bromo-4-fluorobenzyl Bromide

HRID 1356803Notes

Reaction equation

HRID 1356803 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[F:8].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[CH2:9][Br:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 967453-Bromo-4-fluorotoluene

Product 1

HCID 129227103-Bromo-4-fluorobenzyl BromideYield 98.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3-Bromo-4-fluorotoluene (9.36 g; 49.5 mmol) was dissolved in carbon tetrachloride (100 ml), and N-bromosuccinimide (8.82 g; 49.6 mmol) and benzoyl peroxide (200 mg) were added thereto. The mixture was heated under reflux for 1 hour, and then cooled. Insoluble matter was filtered off, followed by washing with carbon tetrachloride. The filtrate was concentrated under reduced pressure, and n-hexane (120 ml) was added thereto. The mixture was left to stand, and insoluble matter was filtered off, followed by washing with n-hexane. The filtrate was evaporated, to thereby yield 13.04 g of a mixture of the target-compound, the starting compound, and the dibromo compound (yield based on the weight of the mixture: 98.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. filtrationInsoluble matter was filtered off
  5. washby washing with carbon tetrachloride
  6. concentrationThe filtrate was concentrated under reduced pressure, and n-hexane (120 ml)
  7. additionwas added
  8. waitThe mixture was left
  9. filtrationinsoluble matter was filtered off
  10. washby washing with n-hexane
  11. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-af826f9230e847e5a9aa798861edcb39
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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