Allyl bromide → HCID 131713232, compound

HRID 1649481Notes

Reaction equation

HRID 1649481 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[C:8]([Cl:16])=[CH:9][C:10]([Cl:15])=[C:11]([CH2:13][OH:14])[CH:12]=1.O1C[CH2:20][CH2:19][CH2:18]1.[H-].[Na+].C(Br)C=C>O>[CH2:20]([O:14][CH2:13][C:11]1[CH:12]=[C:7]([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]([Cl:16])=[CH:9][C:10]=1[Cl:15])[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 70522272HCID 70522272, compound

Product 1

HCID 131713232HCID 131713232, compound

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 5.10 gm of the 5-pyrimidyl-2,4-dichlorophenylcarbinol and 100 of anhydrous tetrahydrofuran. The system was cooled to 0° C. and after cooling 0.53 gm sodium hydride added. The system was stirred for 20 additional minutes and 2.1 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 2 hours. Afterwards the system was heated at reflux for 17 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 5.47 gm of the 5-pyrimidyl-2,4-dichlorophenylcarbinol allylether as an orange liquid and listed as Compound No. 2, 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 17 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-ab5265eb90b94f4cb48347291a549ad0
Source dataset
uspto-grants-1983_11
Patent number
US04417050

Reaction notes

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