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1-Bromohexane → HCID 14745781, compound

HRID 358810
Notes
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Reaction equation

HRID 358810 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][CH:16]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[K].CC(C)([O-])C.[CH2:34](Br)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].C(OCC)(=O)C>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81011-BromohexaneHCID 8857Ethyl AcetateHCID 50987170Potassium tertbutoxideHCID 135736655HCID 135736655, compound

Product 1

HCID 14745781HCID 14745781, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

0.5 g of 2-(3-fluoro-4-hydroxyphenyl)-5-(4-heptylphenyl)pyrimidine and 0.185 g of potassium-tertbutoxide were dissolved in 20 ml of dimethyl sulfoxide. The resulting solution was stirred at room temperature for 30 minutes and then 0.295 of n-hexyl bromide was added dropwise thereto. After the completion of the addition, the mixture was stirred at room temperature for six hours. Then 100 ml of ethyl acetate and 100 ml of water were added to the reaction mixture and the organic layer was repeatedly washed with water until the pH value of the aqueous layer became neutral. Subsequently the organic layer was separated and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (developing solvent: toluene) and then recrystallized from ethanol. Thus 0.467 g of 2-(3-fluoro-4-hexyloxyphenyl)-5-(4-heptylphenyl)pyrimidine was obtained. Yield: 74%.

Workup

  1. additionAfter the completion of the addition
  2. stirringthe mixture was stirred at room temperature for six hours
  3. washthe organic layer was repeatedly washed with water until the pH value of the aqueous layer
  4. customSubsequently the organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel column chromatography (developing solvent: toluene)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-aa0538b45f0243d4a972d5de8f2bbe54
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04997942

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes