Benzyl Bromide → HCID 59256698, compound

HRID 640794Notes

Reaction equation

HRID 640794 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[N:8]=[CH:7][C:6]([CH3:13])=[N:5][C:4]=2[C:3]=1[OH:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[K+]>CCO>[CH2:15]([O:14][C:3]1[C:2]([Cl:1])=[CH:11][C:10]([Cl:12])=[C:9]2[C:4]=1[N:5]=[C:6]([CH3:13])[CH:7]=[N:8]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 135412675HCID 135412675, compound

Product 1

HCID 59256698HCID 59256698, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6,8-dichloro-3-methylquinoxalin-5-ol (150 mg, 0.655 mmol), benzyl bromide (0.20 mL, 1.68 mmol), KOH (0.09 g) and EtOH (10 mL) was heated under reflux for 16 h, cooled, and concentrated. Dichloromethane (20 mL) was added and the mixture washed with H2O (5 mL×2), dried and concentrated. The residue was purified via SiO2-gel chromatography (dichloromethane/MeOH, 1:0-150:1) to give 8-benzyloxy-5,7-dichloro-2-methylquinoxaline (98 mg, 47%).—1H NMR (CDCl3): δ 8.82 (s, 1H), 7.81 (s, 1H), 7.58 (m, 2H), 7.38 (m, 2H), 5.45 (s, 2H), 2.85 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. additionDichloromethane (20 mL) was added
  6. washthe mixture washed with H2O (5 mL×2)
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified via SiO2-gel chromatography (dichloromethane/MeOH, 1:0-150:1)

Sources & evidence

ORD record
ord-a0ecb9e73bea402a8bb68527d738a5b6
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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