Allyl bromide → 2-(Allyloxy)-1-bromo-5-methyl-3-nitrobenzene

HRID 1373766

Reaction equation

HRID 1373766 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O:12][C:3]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Br:1])[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 299182-Bromo-4-methyl-6-nitrophenol

Product 1

HCID 149774442-(Allyloxy)-1-bromo-5-methyl-3-nitrobenzeneYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-bromo-4-methyl-6-nitrophenol (7.00 g, 30.2 mmol), K2CO3 (6.26 g, 45.3 mmol) in acetone (105 mL) was added allyl bromide (3.80 ml, 45.3 mmol). The reaction mixture was stirred at room temperature overnight. It was then heated at 40° C. for 5 hrs. Inorganic salts were filtered and washed with acetone. The filtrate was concentrated to give 7.74 g (94%) of the desired product. MS (DCI/NH3) m/z: 289.0 (M+NH4)+; 1H NMR (300 MHz, CD3OD) δ ppm 2.37 (s, 3 H) 4.61 (d, J=6.10 Hz, 2 H) 5.26 (dd, J=10.51, 1.80 Hz, 1 H) 5.39 (dd, J=17.29, 1.80 Hz, 1 H) 6.09 (m, 1 H) 7.63 (s, 1 H) 7.74 (s, 1 H).

Workup

  1. temperatureIt was then heated at 40° C. for 5 hrs
  2. filtrationInorganic salts were filtered
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-45249ef8d80d45258c2767c58c8dce87
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Linked notes

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