1-Fluoro-2-nitrobenzene → HCID 22504165, compound

HRID 1814291Notes

Reaction equation

HRID 1814291 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][CH:13]([OH:15])[CH3:14].CC(C)([O-])C.[K+].F[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][CH:13]([O:15][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])[CH3:14]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 22504181HCID 22504181, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22504165HCID 22504165, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Methyl-naphthalen-1-yl)-propan-2-ol (1.2 g, 6.0 mmol) was dissolved in freshly distilled THF (15 mL) in a round bottom flask fitted with a reflux condenser. Potassium tert-butoxide (739 mg, 6.60 mmol) was added and the reaction was stirred at room temperature for 30 minutes. 2-fluoronitrobenzene (0.70 mL, 6.60 mmol) was added via syringe. The reaction was stirred at vigorous reflux for 18 hours. The reaction mixture was allowed to cool to room temperature and then was concentrated. The residue was diluted with saturated aqueous NaHCO3 and was extracted three times with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 20% CH2Cl2-hexanes) to give 2-methyl-1-[2-(2-nitro-phenoxy)-propyl]-naphthalene (1.51 g, 4.72 mmol) in 79% yield as an oil that solidified on standing. 1H NMR (300 MHz) CDCl3 δ 8.03 (d, J=8.4 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.67 (m, 2H), 7.49 (m, 1H), 7.40 (m, 1H), 7.29 (m, 2H), 6.90 (m, 1H), 6.75 (d, J=8.6 Hz, 1H), 4.93 (m, 1H), 3.67 (dd, J=7.5, 14.5 Hz, 1H), 3.46 (dd, J=5.7, 14.4 Hz, 1H), 2.56 (s, 3H), 1.46 (d, J=6.0 Hz, 3H).

Workup

  1. customfitted with a reflux condenser
  2. stirringThe reaction was stirred
  3. temperatureat vigorous reflux for 18 hours
  4. temperatureto cool to room temperature
  5. concentrationwas concentrated
  6. additionThe residue was diluted with saturated aqueous NaHCO3
  7. extractionwas extracted three times with EtOAc
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered through celite
  11. concentrationconcentrated
  12. customThe crude product was purified by flash chromatography (SiO2, 20% CH2Cl2-hexanes)

Sources & evidence

ORD record
ord-d1f7edaee5ed4307bb2076a5d7edf90d
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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