Boron tribromide → HCID 68657033, compound

HRID 2281069Notes

Reaction equation

HRID 2281069 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, 1 M 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 treated with sodium hydroxide (1 N 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 and 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. additiontreated with sodium hydroxide (1 N aqueous) until pH>10
  4. stirringAfter stirring for an additional 30 minutes
  5. additionammonium chloride (aqueous saturated) was added until the pH of the mixture
  6. extractionThe aqueous mixture was extracted exhaustively with dichloromethane containing 5% methanol
  7. dry with materialthe combined organic extracts were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a12275bd628947ed99eb9ec5d29cad6d
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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