Benzyl Bromide → 5-Benzyloxy-2-chloro-nitrobenzene

HRID 1879529Notes

Reaction equation

HRID 1879529 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 110436225-Benzyloxy-2-chloro-nitrobenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To 4-chloro-3-nitrophenol (1.74 g, 10 mmol) and benzyl bromide (2.05 g, 12 mmol) in 25 mL of acetone was added K2CO3 (2.76 g, 20 mmol). The mixture was heated at 60° C. for 4 h under Ar atmosphere and cooled to rt. It was filtered and the solid was washed with ether (80 mL) and the combined filtrate was concentrated and chromatographed (EtOAc in hexane, 3% to 30% gradient) to afford 4-(benzyloxy)-1-chloro-2-nitrobenzene as a light-yellow solid (2.5 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=2.8 Hz, 1H), 7.42-7.34 (m, 5H), 7.11 (dd, J=8.8, 2.8 Hz, 1H), 5.08 (s, 2H); MS (ESI) m/z 264 (M+H+).

Workup

  1. temperaturecooled to rt
  2. filtrationIt was filtered
  3. washthe solid was washed with ether (80 mL)
  4. concentrationthe combined filtrate was concentrated
  5. customchromatographed (EtOAc in hexane, 3% to 30% gradient)

Sources & evidence

ORD record
ord-51138e1d1c194b02aeea732393182576
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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