Iodine → HCID 18513409, compound

HRID 321894Notes

Reaction equation

HRID 321894 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Li]C(CC)C.[I:24]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[I:24]

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 18513411HCID 18513411, compoundHCID 178418400CID 53628100

Product 1

HCID 18513409HCID 18513409, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

In a solution of 4.8 g (19.7 mmol) of the 3-fluoro-(2-(4-propylphenyl)ethyl)benzene obtained in the previous step in 25 ml of THF was added dropwise 23 ml of sec-BuLi (1.04 M, cyclohexane solution, corresponding to 23.7 mmol) while being maintained at a temperature lower than −60° C., and they were stirred at the same temperature for 1 hour. Subsequently, a solution of 7.5 g (29.6 mmol) of iodine in 20 ml of THF was added dropwise to the reaction mixture while being maintained at a temperature lower than −60° C., and they were stirred at the same temperature for 1 hour. The reaction solution was poured into 50 ml of a diluted aqueous sodium thiosulfate solution, and extracted with 50 ml of heptane. The organic layer thus obtained was washed with water thrice and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under a reduced pressure, the residue was subjected to silica gel column chromatography (eluent: heptane) to obtain 6.5 g of a crude 3-fluoro-4-iodo-(2-(4-propylphenyl)ethyl)benzene. This product was used for next reaction without any further purification. (Yield: 90.2%)

Workup

  1. temperaturewhile being maintained at a temperature lower than −60° C.
  2. stirringthey were stirred at the same temperature for 1 hour
  3. extractionextracted with 50 ml of heptane
  4. customThe organic layer thus obtained
  5. washwas washed with water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-e5ca6d75c50449f59f2a161d3174ce1e
Source dataset
uspto-grants-2001_04
Patent number
US06210603B1

Reaction notes

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