Iodine → 1-Iodo-4-(pentylthio)benzene

HRID 1440178Notes

Reaction equation

HRID 1440178 reaction equation
[CH2:1]([S:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].[I:15]I.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[CH2:1]([S:6][C:7]1[CH:12]=[CH:11][C:10]([I:15])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 807IodineHCID 656671Sodium PyrosulfiteHCID 5462224MagnesiumHCID 125212421-Bromo-4-(pentylsulfanyl)benzene

Product 1

HCID 189826561-Iodo-4-(pentylthio)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent from the product of Step 2.1 (15 g) was prepared using magnesium in tetrahydrofuran (60 ml). Iodine (16.2 g) was added over 10 min and the mixture was stirred for 16 hrs. Water was added and then 10% sodium metabisulphite (100 ml). The product was extracted into petroleum ether and distilled. Yield 10.5 g.

Workup

  1. extractionThe product was extracted into petroleum ether
  2. distillationdistilled

Sources & evidence

ORD record
ord-c57a66ec3d16498ea0dbb64e58dc142c
Source dataset
uspto-grants-1996_03
Patent number
US05498366

Reaction notes

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