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Ethyl Acetate → 2-Chloro-6-(2-fluorophenyl-oxy)-pyrazine

HRID 16276
Notes
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Reaction equation

HRID 16276 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].CCOC(C)=O>C1CCCCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])[N:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 97072-FluorophenolHCID 785042,6-Dichloropyrazine

Product 1

HCID 593434982-Chloro-6-(2-fluorophenyl-oxy)-pyrazineYield 80%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Using Method DD with 2,6-dichloropyrazine (250 mg, 1.69 mmol) and 2-fluorophenol (166 μL, 1.86 mmol, d=1.26 g/mL), and purification by column chromatography (AcOEt:cyclohexane, 1:1), the title compound was obtained (302 mg). Yield: 80%. 1H NMR (250 MHz, DMSO-d8) δ 7.31-7.45 (m, 4H, Harom), 8.56 (s, 1H, HPz 5), 8.67 (s, 1H, HPz 3).

Sources & evidence

ORD record
ord-84f417115a524c49a82fcdcb077d715b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737152B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes