Boron tribromide → HCID 67606759, compound

HRID 1626971Notes

Reaction equation

HRID 1626971 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15]C.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67606434HCID 67606434, compound

Product 1

HCID 67606759HCID 67606759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-1-(cyclopropylmethyl)-5-methoxy-1H-benzotriazole (8.0 g, 28 mmol) was dissolved in dichloromethane (200 mL), cooled to 0° C. and treated with boron tribromide (57 mL, 1 M dichloromethane solution, 57 mmol, 2 equiv). The ice bath was removed and the mixture was warmed to ambient temperature and stirred for 4 hours. The mixture was treated slowly with water (exotherm), the pH of the solution was adjusted to pH>10 with 1 N aqueous sodium hydroxide and stirred for an additional 30 minutes. The pH of the mixture was then adjusted to pH 6-7 with ammonium chloride (aqueous saturated) and extracted exhaustively with dichloromethane containing 5% methanol. The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. customThe ice bath was removed
  2. temperaturethe mixture was warmed to ambient temperature
  3. additionThe mixture was treated slowly with water (exotherm)
  4. stirringstirred for an additional 30 minutes
  5. extractionextracted exhaustively with dichloromethane containing 5% methanol
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15103ac3bf4f46058bdff8e55ca32a26
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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