2,6-Lutidine → 1-(3-Bromopropyl)-4-nitrobenzene

HRID 856725Notes

Reaction equation

HRID 856725 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12]O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC1C=CC=C(C)N=1.CS(OS(C)(=O)=O)(=O)=O.[Br-:31].[Li+]>C1COCC1.C(OCC)(=O)C.O>[Br:31][CH2:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 79372,6-LutidineHCID 81560Methanesulfonic anhydrideHCID 82050Lithium BromideHCID 134230513-(4-Nitrophenyl)propan-1-ol

Product 1

HCID 104444821-(3-Bromopropyl)-4-nitrobenzeneYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

3-(4-nitrophenyl)propanol (5.0 g) was dissolved in THF (100 ml), 2,6-dimethylpyridine (5.1 ml) and methanesulfonic acid anhydride (6.7 g) were added to the mixture, and the mixture was stirred for 12 hours at 50° C. Lithium bromide (3.6 g) was added to the mixture, and the mixture was stirred for 8 hours at 60° C. After cooling to room temperature, the reaction solution was added to water, and dissolved in ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 1-(3-bromopropyl)-4-nitrobenzene (3.1 g).

Workup

  1. stirringthe mixture was stirred for 8 hours at 60° C
  2. temperatureAfter cooling to room temperature
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-46b55b5cb4174dbb97a483d2afe271d2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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