Boron tribromide → HCID 68657033, compound

HRID 1618931Notes

Reaction equation

HRID 1618931 reaction equation
[Cl: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>[Cl: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 68656860HCID 68656860, compound

Product 1

HCID 68657033HCID 68657033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-1-(cyclopropylmethyl)-5-methoxy-1H-benzotriazole (10.5 g, 44.2 mmol) was dissolved in dichloromethane (200 mL), cooled to 0° C. and treated with boron tribromide (88 mL, 1M dichloromethane solution, 88 mmol, 2 equiv). The ice bath was removed and the mixture was stirred for 4 hours at ambient temperature. The mixture was treated with water (10 mL) and then sodium hydroxide (1N aqueous) until pH>10. After stirring for an additional 30 minutes, ammonium chloride (aqueous saturated) was added until the pH of the mixture was adjusted to pH 6-7. The aqueous mixture was 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 as a light brown solid.

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was treated with water (10 mL)
  3. stirringAfter stirring for an additional 30 minutes
  4. additionammonium chloride (aqueous saturated) was added until the pH of the mixture
  5. extractionThe aqueous mixture was extracted 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-f444b562fdf74c698f27ec0d3c44270c
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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