1-Bromononane → 2-(3-Fluoro-4-n-nonyloxyphenyl)-5-(4-n-hexylphenyl)pyrazine

HRID 358805Notes

Reaction equation

HRID 358805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:16]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[K].CC(C)([O-])C.[CH2:33](Br)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CS(C)=O.O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:16]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 3

HCID 127421-BromononaneHCID 50987170Potassium tertbutoxideHCID 1357366542-(3-Fluoro-4-hydroxyphenyl)-5(4-n-hexylphenyl)pyrazine

Product 1

HCID 147161002-(3-Fluoro-4-n-nonyloxyphenyl)-5-(4-n-hexylphenyl)pyrazineYield 86.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.35 g of the crude 2-(3-fluoro-4-hydroxyphenyl)-5-(4-n-hexylphenyl)pyrazine was dissolved in 3 ml of dimethyl sulfoxide and 3 ml of tetrahydrofuran. To the resulting solution, was added 0.12 g of potassium-tertbutoxide. The obtained mixture was stirred at room temperature for 30 minutes and then 0.22 g of n-nonyl bromide was added thereto. The mixture was stirred at room temperature for additional five hours. Then the reaction mixture was diluted with ethyl acetate, washed with dilute hydrochloric acid and with a 30% aqueous solution of sodium hydroxide and then repeatedly washed with water until the washing liquor showed a pH value of approximately 7. Then the ethyl acetate phase was dehydrated over sodium sulfate and the solvent was distilled off. Thus 0.48 g of a crude reaction product was obtained. The crude reaction product was purified by silica gel column chromatography and recrystallized from acetone. Thus 0.41 g of the title compound was obtained. Phase transition temperature: 93.0° C. (C→Sc);

Workup

  1. stirringThe mixture was stirred at room temperature for additional five hours
  2. washwashed with dilute hydrochloric acid and with a 30% aqueous solution of sodium hydroxide
  3. washrepeatedly washed with water until the washing liquor
  4. distillationthe solvent was distilled off
  5. customThus 0.48 g of a crude reaction product
  6. customwas obtained
  7. customThe crude reaction product
  8. customwas purified by silica gel column chromatography
  9. customrecrystallized from acetone

Sources & evidence

ORD record
ord-c790fa4799c042beae8f97d175a1fe23
Source dataset
uspto-grants-1991_03
Patent number
US04997942

Reaction notes

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