Water → HCID 67190633, compound

HRID 515299Notes

Reaction equation

HRID 515299 reaction equation
[Cl: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.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[Cl:1]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 103524921-Chloro-4-fluoro-2-methyl-5-nitrobenzene

Product 1

HCID 67190633HCID 67190633, compoundYield 109.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

1-Chloro-4-fluoro-2-methyl-5-nitrobenzene (1 g) was dissolved in chlorobenzene (6 mL) and N-bromosuccinimide (1.408 g) was added followed by benzoyl peroxide (0.183 mg). The reaction mixture was stirred at reflux for 4 hours. The reaction mixture was cooled and water was added. The mixture was extracted with dichloromethane (3×) and concentrated under reduced pressure. The crude oil obtained was triturated with diethyl ether, filtered and the filtrate concentrated under reduced pressure (3×) to yield the title compound (1.55 g).

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude oil obtained
  6. customwas triturated with diethyl ether
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure (3×)

Sources & evidence

ORD record
ord-fa61ed9c883743d1a4e3c91623bed79a
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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