4-Hydroxybiphenyl → 2-Chloro-6-(4-phenyl-phenyl-oxy)-pyrazine

HRID 16283

Reaction equation

HRID 16283 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]1([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOC(C)=O.C1CCCCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:21][C:18]2[CH:17]=[CH:16][C:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:20][CH:19]=2)[N:3]=1

Participants

5

Reactant 2

HCID 71034-HydroxybiphenylHCID 785042,6-Dichloropyrazine

Product 1

HCID 593434952-Chloro-6-(4-phenyl-phenyl-oxy)-pyrazineYield 99%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using Method DD (reaction time: 20 hours) with 2,6-dichloropyrazine (200 mg, 1.34 mmol) and 4-phenyl-phenol (268 mg, 1.49 mmol), and purification by column chromatography (AcOEt:cyclohexane, 1:2), the title compound was obtained (376 mg). Yield: 99%. 1H NMR (250 MHz, DMSO-d6) δ 7.40-7.60 (m, 5H, Harom), 7.76 (d, 2H, Harom 3+5, J=7.1 Hz), 7.82 (d, 2H, Harom 2+6, J=8.7 Hz), 8.59 (s, 1H, HPz 5), 8.65 (s, 1H, HPz 3). m/z: 283.1 [(M+H)+, calcd for C16H11ClN2O 282.1].−

Workup

  1. customMethod DD (reaction time: 20 hours)

Sources & evidence

ORD record
ord-853c027b980d4cdf9f350bbb2b0b6699
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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