Allyl bromide → 1-(Allyloxy)-4-methyl-2-nitrobenzene

HRID 1373765Notes

Reaction equation

HRID 1373765 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CC(C)=O>[CH2:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 83914-Methyl-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 210753571-(Allyloxy)-4-methyl-2-nitrobenzeneYield 88.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-methyl-2-nitro-phenol (1.50 g, 9.80 mmol) and K2CO3 (2.03 g, 14.7 mmol) in acetone (23 mL) was added allyl bromide (1.24 ml, 14.7 mmol). The reaction mixture was stirred at room temperature overnight. It was then heated at 40° C. for 6 hrs. Inorganic salts were filtered and washed with acetone. The filtrate was concentrated and the residue was purified by flash chromatograph eluting with hexane/EtOAc (95:5) to give 1.67 g (88%) of the desired product. MS (DCI/NH3) m/z: 211.0 (M+NH4)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 2.30 (s, 3 H) 4.67–4.75 (m, 2 H) 5.27 (m, 1 H) 5.42 (m, 1 H) 5.97 (m, 1 H) 7.24 (d, J=8.48 Hz, 1 H) 7.45 (dd, J=8.65, 2.20 Hz, 1 H) 7.69 (d, J=2.37 Hz, 1 H).

Workup

  1. temperatureIt was then heated at 40° C. for 6 hrs
  2. filtrationInorganic salts were filtered
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash chromatograph
  6. washeluting with hexane/EtOAc (95:5)

Sources & evidence

ORD record
ord-5b6574bd8ec54d599a434615454b2e26
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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