Allyl bromide → 3-{(2,4-Dichlorophenyl)[(prop-2-en-1-yl)oxy]methyl}pyridine

HRID 647087Notes

Reaction equation

HRID 647087 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[OH:8])[CH:2]=1.O1C[CH2:20][CH2:19][CH2:18]1.[H-].[Na+].C(Br)C=C>O>[CH2:20]([O:8][CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 13236916HCID 13236916, compound

Product 1

HCID 132369173-{(2,4-Dichlorophenyl)[(prop-2-en-1-yl)oxy]methyl}pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 ml single neck round bottom flask equipped with a reflux condensor and an argon inlet was added 3.56 gm of the 3-pyridyl-2,4-dichlorophenylcarbinol and 60 ml of anhydrous tetrahydrofuran. The system was cooled to 0° C. and after cooling 0.37 gm sodium hydride added. The system was stirred for 75 additional minutes and 1.45 ml of allyl bromide was then added. The system was allowed to come to room temperature over 1/2-hour and stirred there for an additional 1 hour. Afterwards the system was heated at reflux for 18 hours. At this time, water was added to the system and the product extracted with methylene chloride. The methylene chloride was then washed with water and then dried over sodium sulfate. The methylene chloride was removed by stripping to give 1.73 gm of the 3-pyridyl-2,4-dichlorophenylcarbinol allylether and listed as compound number 3 in Table I.

Workup

  1. customTo a 250 ml single neck round bottom flask equipped with a reflux condensor and an argon inlet
  2. additionadded
  3. additionwas then added
  4. waitto come to room temperature over 1/2-hour
  5. temperatureAfterwards the system was heated
  6. temperatureat reflux for 18 hours
  7. extractionthe product extracted with methylene chloride
  8. washThe methylene chloride was then washed with water
  9. dry with materialdried over sodium sulfate
  10. customThe methylene chloride was removed

Sources & evidence

ORD record
ord-7c446d07006f43a7a418cb0f6a54befc
Source dataset
uspto-grants-1983_10
Patent number
US04407806

Reaction notes

Loading…