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1-Bromo-4-fluorobenzene → alpha,alpha-Bis(4-fluorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol

HRID 1193631
Notes
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Reaction equation

HRID 1193631 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.C(O[C:13]([CH:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:17][CH2:16]1)=[O:14])C.[Cl-].[NH4+]>O1CCCC1>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:13]([C:3]2[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=2)([CH:15]2[CH2:16][CH2:17][N:18]([S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)(=[O:22])=[O:23])[CH2:19][CH2:20]2)[OH:14])=[CH:4][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 257103Ethyl 1-(phenylsulfonyl)piperidine-4-carboxylateHCID 5462224Magnesium

Product 1

HCID 14407073alpha,alpha-Bis(4-fluorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a suspension of 33.78 g (1.39 mole) of magnesium trimmings in 1 liter of tetrahydrofuran (dried over molecular sieves 5A) under an atmosphere of N2 and cooled in an ice bath was added dropwise a solution of 243.25 g (1.39 mole) of p-bromofluorobenzene in 150 ml of tetrahydrofuran. The mixture was stirred for 2 hr after the addition was completed. To this mixture was added 103 g (0.346 mole) of 1-(phenylsulfonyl)-4-piperidinecarboxylic acid ethyl ester as a solid, and the solution was stirred at ambient temperature for 5 hr. The reaction was poured into an icy aqueous solution of ammonium chloride. The phases were separated, and the solvent was removed in vacuo from the organic phase. The residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate and was reduced in vacuo to ≅1 liter volume. The title compound was obtained by adding hexane and cooling, recrystallizing the precipitate from ethyl acetate and hexane and drying the solid under high vacuum at 130° C. for 45 min. at which time the product had partially melted, m.p. 142.5°-144° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionafter the addition
  3. stirringthe solution was stirred at ambient temperature for 5 hr
  4. customThe phases were separated
  5. customthe solvent was removed in vacuo from the organic phase
  6. customThe residue was partitioned between methylene chloride and dilute sodium hydroxide
  7. dry with materialThe methylene chloride solution was dried over magnesium sulfate

Sources & evidence

ORD record
ord-1e96cda3aef94e9e8932f09f5e3e91d3
Source dataset
uspto-grants-1989_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04810713

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes