Allyl bromide → HCID 68195083, compound

HRID 2370657Notes

Reaction equation

HRID 2370657 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CC(C)=O>[CH2:20]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Cl:1])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 3013917Phenol, 2-chloro-3-nitro-

Product 1

HCID 68195083HCID 68195083, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-chloro-3-nitrophenol (1.5 g, 8.64 mmol) in acetone was added potassium carbonate (1.194 g, 8.64 mmol). After 5 minutes, allyl bromide (0.823 ml, 9.51 mmol) was added and the solution was heated to reflux overnight. The reaction mixture was cooled, filtered, and concentrated. Chromatography was performed with an Analogix 280 with an SF 40-80 column, 0% to 10% ethyl acetate/hexane gradient over 30 minutes to provide the title compound. MS (DCI+) m/z 231.1 (M+NH4)+.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. waitChromatography was performed with an Analogix 280 with an SF 40-80 column, 0% to 10% ethyl acetate/hexane gradient over 30 minutes

Sources & evidence

ORD record
ord-9f12533c5b4a41538904d6b871f40216
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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