Boron tribromide → HCID 136364208, compound

HRID 1471344Notes

Reaction equation

HRID 1471344 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[C:5]([CH3:14])=[N:4][N:3]=1.B(Br)(Br)Br>ClCCl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[C:5]([CH3:14])=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 576916544-Chloro-6-methoxy-1-methylphthalazine

Product 1

HCID 136364208HCID 136364208, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-chloro-6-methoxy-1-methylphthalazine (4) (2.08 g, 9.99 mmol), 1.0 M boron tribromide (17.00 mmol) in dichloromethane (17 mL), and dichloromethane (50 mL) is stirred under argon at −78° C. for 10 min, room temperature for 38 h, and at reflux for 3 h. The mixture is cooled to room temperature, diluted with sat. NaHCO3 (130 mL), and extracted with ethyl acetate (150 mL and 4×60 mL). The extract is washed (water and brine) and dried. After solvent removal at reduced pressure, the remaining solid is washed with dichloromethane to give 650 mg (70%) of 5 as a yellow solid, mp >260° C. IR 3351, 2938, 1610, 1223 cm−1; 1H NMR (DMSO-d6) δ 2.84 (s, 3H, CH3), 7.44 (d, J=8.7 Hz, 1H, 8-PhthH), 7.59 (dd, J=9.0, 2.4 Hz, 1H, 6-PhthH), 8.19 (d, J=9.0 Hz, 1H, 5-PhthH), 11.27 ppm (s, 1H, OH).

Workup

  1. temperatureat reflux for 3 h
  2. extractionextracted with ethyl acetate (150 mL and 4×60 mL)
  3. washThe extract is washed (water and brine)
  4. customdried
  5. customAfter solvent removal at reduced pressure
  6. washthe remaining solid is washed with dichloromethane

Sources & evidence

ORD record
ord-e8e5ad9da9b942c895b1ce02d5cbb891
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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