Iodine → HCID 23036471, compound

HRID 1709857Notes

Reaction equation

HRID 1709857 reaction equation
[Mg].II.Br[C:5]1[CH:6]=[C:7]([F:11])[CH:8]=[CH:9][CH:10]=1.C1(S([N:21]2[CH2:31][CH2:30][CH:24](C(OCC)=O)[CH2:23][CH2:22]2)(=O)=O)C=CC=CC=1.[Cl-].[NH4+].CC[O:36][CH2:37][CH3:38]>O1CCCC1>[F:11][C:7]1[CH:6]=[C:5]([C:37]([C:38]2[CH:10]=[CH:5][CH:6]=[C:7]([F:11])[CH:8]=2)([N:21]2[CH2:22][CH2:23][CH2:24][CH2:30][CH2:31]2)[OH:36])[CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 6

HCID 807IodineHCID 3283Diethyl Ether2×HCID 140821-Bromo-3-fluorobenzeneHCID 25517Ammonium ChlorideHCID 257103Ethyl 1-(phenylsulfonyl)piperidine-4-carboxylateHCID 5462224Magnesium

Product 1

HCID 23036471HCID 23036471, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7.78 g (0.33 mole) of magnesium turnings and a crystal of iodine in 800 ml of anhydrous ether under an atmosphere of nitrogen atmosphere was slowly added a solution of 3-bromofluorobenzene in 200 ml of ether. The mixture was stirred for 1.5 hr and 30.6 g (0.103 mole) of ethyl 1-benzenesulfonylisonipecotate was added as a solid. Tetrahydrofuran (300 ml)was added, and the mixture was stirred at room temperature for 12 hr. The mixture was poured into an icy solution of ammonium chloride. The aqueous mixture was extracted with methylene chloride, and the resulting residue was recrystallized from ether to give 24.14 g (52.9%) of the title compound as a white, crystalline solid, m.p. 183°-185° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionThe aqueous mixture was extracted with methylene chloride
  3. customthe resulting residue was recrystallized from ether

Sources & evidence

ORD record
ord-49298aa4b661443591a917abf4ea83c9
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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