Bromine → 5-Nitro-2-bromoindan-1-one

HRID 2290223Notes

Reaction equation

HRID 2290223 reaction equation
[Br:1]Br.[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9]2)([O-:5])=[O:4]>C(Cl)(Cl)Cl.CO>[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH:10]([Br:1])[CH2:9]2)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 123412855-Nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 202319935-Nitro-2-bromoindan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

Bromine (1.79 ml) in chloroform (125 ml) was added dropwise over 15 minutes to a stirred solution of 5-nitroindan-1-one (6.17 g) in chloroform (200 ml) at 5° C. The stirred solution was allowed to warm to room temperature and after one hour, when the bromine colour had discharged, the solution was washed with water and dried. Evaporation of the filtered solution under reduced pressure afforded an oil which was diluted with methanol and crystallised (with seeding) to give 5-nitro-2-bromoindan-1-one, m.p. 88.5°-90.5° C. (recrystallised from methanol).

Workup

  1. washthe solution was washed with water
  2. customdried
  3. customEvaporation of the filtered solution under reduced pressure
  4. customafforded an oil which
  5. customcrystallised (with seeding)
  6. customto give
  7. custom5-nitro-2-bromoindan-1-one, m.p. 88.5°-90.5° C. (recrystallised from methanol)

Sources & evidence

ORD record
ord-8813f339d6b5446594113270a4b22cbc
Source dataset
uspto-grants-1986_10
Patent number
US04616013

Reaction notes

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