Sodium Hydroxide → HCID 66667026, compound

HRID 1049672Notes

Reaction equation

HRID 1049672 reaction equation
[CH2:1]([C:3]1([CH2:7][O:8][CH:9]=[CH2:10])[CH2:6][O:5][CH2:4]1)[CH3:2].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.B1C2CCCC1CCC2.[C:40]1([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH:45]=[CH:44][CH:43]=[C:42]([C:46]2[N:51]=[C:50]([C:52]3[CH:53]=[C:54]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[CH:55]=[CH:56][CH:57]=3)[N:49]=[C:48]([C:64]3[CH:69]=[CH:68][CH:67]=[C:66](Br)[CH:65]=3)[N:47]=2)[CH:41]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:40]1([C:71]2[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=2)[CH:45]=[CH:44][CH:43]=[C:42]([C:46]2[N:51]=[C:50]([C:52]3[CH:53]=[C:54]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[CH:55]=[CH:56][CH:57]=3)[N:49]=[C:48]([C:64]3[CH:65]=[CH:66][CH:67]=[C:68]([CH2:10][CH2:9][O:8][CH2:7][C:3]4([CH2:1][CH3:2])[CH2:6][O:5][CH2:4]4)[CH:69]=3)[N:47]=2)[CH:41]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 66666456HCID 66666456, compoundHCID 66666479HCID 66666479, compound

Product 1

HCID 66667026HCID 66667026, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.1 g (92 mmol) of 3-ethyl-3-vinyloxymethyloxetane and 11.3 g (60.8 mmol) of 9-BBN dimer are dissolved in 200 ml of toluene at room temperature under protective gas and stirred for 20 h. During the reaction, the suspension of 9-BBN slowly dissolves. 50 g (92 mmol) of 2,4-bis-biphenyl-3-yl-6-(3-bromophenyl)-1,3,5-triazine and 50 ml of a 1 M NaOH solution are subsequently added to the reaction solution. The reaction mixture is carefully degassed, 200 mg of tetrakistriphenylphosphino-palladium are added, and the mixture is heated under reflux for 20 h. The solution is cooled to room temperature, and the phases are separated. The aqueous phase is extracted three times with toluene, the combined organic phases are subsequently washed twice with water, dried over magnesium sulfate, filtered, and the solvent is stripped off in vacuo. The residue is recrystallised from ethanol/toluene 3:1, giving 54 g (89 mmol) (97%) of a white solid in a purity of 99:8%.

Workup

  1. customDuring the reaction
  2. dissolutionslowly dissolves
  3. customThe reaction mixture is carefully degassed
  4. addition200 mg of tetrakistriphenylphosphino-palladium are added
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 20 h
  7. customthe phases are separated
  8. extractionThe aqueous phase is extracted three times with toluene
  9. washthe combined organic phases are subsequently washed twice with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customThe residue is recrystallised from ethanol/toluene 3:1

Sources & evidence

ORD record
ord-b2bc22fed1c94910abfdec78a6f1be20
Source dataset
uspto-grants-2016_07
Patent number
US09382253B2

Reaction notes

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