Boron tribromide → HCID 67011299, compound

HRID 467434Notes

Reaction equation

HRID 467434 reaction equation
[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([N:7]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:30]C)[CH:26]=3)[CH:21]=2)[C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18]C)[CH:14]=3)[CH:9]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([CH3:32])[CH:2]=[CH:3][C:4]([N:7]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([OH:30])[CH:26]=3)[CH:21]=2)[C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=3)[CH:9]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67011429HCID 67011429, compound

Product 1

HCID 67011299HCID 67011299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a reaction vessel equipped with an agitator, thermometer and a cooling pipe, 2.1 g of p-tolyl-bis(6-methoxy-2-naphthyl)amine and 50 mL of methylene chloride were placed. While the vessel was being cooled with ice, 12 mL of a 1M methylene chloride solution of boron tribromide was delivered by drops into the vessel, and the mixture was reacted at the same temperature for one hour. The temperature was raised to a room temperature and further reacted for one hour. Then, the reacted solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and separated, and it was then dried with magnesium sulfate and subjected to vacuum concentration. Thus, the objective product was obtained with the yield of 2.38 g.

Workup

  1. customIn a reaction vessel equipped with an agitator
  2. customthe mixture was reacted at the same temperature for one hour
  3. customfurther reacted for one hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customseparated
  7. dry with materialit was then dried with magnesium sulfate
  8. concentrationsubjected to vacuum concentration
  9. customThus, the objective product was obtained with the yield of 2.38 g

Sources & evidence

ORD record
ord-76e27b87190741a5b724e9b4411db060
Source dataset
uspto-grants-2014_01
Patent number
US08623577B2

Reaction notes

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