Iodine → 2-Iodo-1-benzothiophene

HRID 1948600Notes

Reaction equation

HRID 1948600 reaction equation
C([Li])CCC.CCCCCC.[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1.[I:21]I.[Li]>CCOCC.O>[I:21][C:13]1[S:12][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=1

Participants

8

Reactant 5

HCID 807IodineHCID 7221Benzo(B)ThiopheneHCID 8058HexaneHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 114709462-Iodo-1-benzothiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Butyllithium 1.6M in hexane (112.5 ml, 180 mmole) and absolute ether (70 ml) were placed in a 500 ml three-necked flask under an argon atmosphere and cooled in an ice bath to 0° C. Benzothiophene (20.1 g, 150 mmole) dissolved in absolute ether (40 ml) was then added dropwise within 30 minutes while cooling with ice and the mixture was stirred for 2.5 hours in an ice bath. The reaction mixture was left overnight in a cold cabinet. Iodine (75.0 g) and absolute ether (50 ml) were placed in a 500 ml capacity 3-necked flask under an argon atmosphere and the solution of the lithium compound was added dropwise while cooling with ice. The reaction mixture was slowly heated to room temperature, hydrolysed with water, washed with sodium thiosulfate solution and the organic phase was dried over sodium sulfate. The reaction solution was then concentrated by evaporation in vacuo and purified by means of flash chromatography with cyclohexane.

Workup

  1. additionwas then added dropwise within 30 minutes
  2. temperaturewhile cooling with ice
  3. waitThe reaction mixture was left overnight in a cold cabinet
  4. temperaturewhile cooling with ice
  5. washwashed with sodium thiosulfate solution
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. concentrationThe reaction solution was then concentrated by evaporation in vacuo
  8. custompurified by means of flash chromatography with cyclohexane

Sources & evidence

ORD record
ord-fbd243f709c745c3bf6144ef34d3ac28
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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