N-bromobutanimide → 1-(Bromomethyl)-2,5-difluoro-4-nitrobenzene

HRID 515305

Reaction equation

HRID 515305 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O>ClC1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 2306581,4-Difluoro-2-methyl-5-nitrobenzene

Product 1

HCID 534033971-(Bromomethyl)-2,5-difluoro-4-nitrobenzeneYield 220.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 7964ChlorobenzeneSolvent

Procedure

1,4-Difluoro-2-methyl-5-nitrobenzene (1 g) was dissolved in chlorobenzene (6 mL) and N-bromosuccinimide (1.54 g) added followed by benzoyl peroxide (0.2 g). The reaction mixture was stirred at reflux for 2.5 hours then additional benzoyl peroxide (0.2 g) and N-bromosuccinimide (1.54 g) were added. The reaction was refluxed for 2 hours then was cooled to room temperature, quenched with water and extracted with dichloromethane (3×). The combined organics were dried and concentrated under reduced pressure. The oil obtained was triturated with diethyl ether, filtered and the filtrate concentrated under reduced pressure to yield the title compound (3.21 g).

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction was refluxed for 2 hours
  3. customquenched with water
  4. extractionextracted with dichloromethane (3×)
  5. customThe combined organics were dried
  6. concentrationconcentrated under reduced pressure
  7. customThe oil obtained
  8. customwas triturated with diethyl ether
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-502793d67fcb49f4b86ae129b0caa852
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Linked notes

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