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Sodium Chloride → HCID 178444267, compound

HRID 1780567
Notes
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Reaction equation

HRID 1780567 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.F[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[N:26]=1.[Cl-].[Na+]>C1C=CC=CC=1.CCCCCC.O1CCCC1.CCOCC>[F:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:15]2[CH:14]=[CH:13][C:12]([C@H:9]3[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]3)=[CH:17][CH:16]=2)[N:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 739342,6-DifluoropyridineHCID 178418339ButyllithiumHCID 178444243HCID 178444243, compound

Product 1

HCID 178444267HCID 178444267, compoundYield 7.9%

Reagents, catalysts & solvents 4

HCID 241
Benzene
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8058HexaneSolvent

Procedure

12.48 g (40.40 mmol) of 4-(trans-4-pentylcyclohexyl)bromobenzene in 30 ml of benzene are stirred with 25.20 ml (40.40 mmol) of a 1.6-molar n-butyllithium solution in hexane at room temperature under argon for 18 hours. The reaction mixture is then slowly added dropwise at 0° C. under argon to a solution of 4.20 g (36.70 mmol) of 2,6-difluoropyridine in 30 ml of tetrahydrofuran. After a reaction time of one hour at 0° C., the mixture is distributed between ether and sodium chloride solution, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and freed from solvent. Purification of the residue by chromatography gives 0.94 g of 2-fluoro-6-[4-(trans-4-pentylcyclohexyl)phenyl]pyridine. ##STR50##

Workup

  1. customAfter a reaction time of one hour
  2. customat 0° C.
  3. washthe organic phase is washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customPurification of the residue by chromatography

Sources & evidence

ORD record
ord-93c68bd28f4f4069aa2357ffa8972804
Source dataset
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05630962

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes