Water → 2-Fluoro-7-methylbenzo[b]thiophene

HRID 649009Notes

Reaction equation

HRID 649009 reaction equation
[CH3:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Cl([F:20])(=O)(=O)=O.O>CCCCCC>[F:20][C:9]1[S:8][C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 64285417-Methyl-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 147804912-Fluoro-7-methylbenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 7 g of 7-methylbenzo[b]thiophene in abs. tetryhydrofuran are added dropwise at -78°, 30 ml of a 1.6M solution of n-butyllithium in hexane. After 20 minutes 5.5 g of perchloryl fluoride are introduced whereby the reaction temperature is maintained below -60°. After 30 minutes at -78° the temperature is slowly raised to 0°. The mixture is then mixed with water and the organic phase separated, washed, dried and concentrated under vacuum. The residue is chromatographed (eluant: n-hexane) to obtain the title compound as an oil.

Workup

  1. additiontetryhydrofuran are added dropwise at -78°
  2. temperatureis maintained below -60°
  3. temperatureAfter 30 minutes at -78° the temperature is slowly raised to 0°
  4. customthe organic phase separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe residue is chromatographed (eluant: n-hexane)

Sources & evidence

ORD record
ord-a9ecdd0c7d1e458796e44f0887a2686f
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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