Phenol → HCID 89782156, compound

HRID 1055989Notes

Reaction equation

HRID 1055989 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[CH:20]=[N:19][C:18]2[C:13](=[C:14]([Cl:21])[CH:15]=[CH:16][CH:17]=2)[N:12]=1>C1COCC1>[Cl:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[C:11]([O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH:20]=[N:19]2

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 106080502,8-dichloroquinoxaline

Product 1

HCID 89782156HCID 89782156, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (60% w/w in mineral oil; 269 mg, 6.72 mmol) was added to a solution of phenol (633 mg, 6.72 mmol) in THF (4.5 ml) at 0° C.; the resulting mixture was stirred for 15 min before 2,8-dichloroquinoxaline (177a, 892 mg, 4.48 mmol, Pharmabridge, Inc., Doylestown, Pa.) in THF (10 ml) was added at 0° C. The mixture was slowly warmed to RT and stirred for 16 h. The crude material was quenched with MeOH and was purified by silica gel (100% hexanes to 20% EtOAc/hexanes) to provide 8-chloro-2-phenoxyquinoxaline (61% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 257.2 (M+1).

Workup

  1. additionwas added at 0° C
  2. customThe crude material was quenched with MeOH
  3. customwas purified by silica gel (100% hexanes to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b2dbc0ac4f634124a5573ec747062588
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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