Diethyl Ether → 3-Fluoro-7-methylbenzo[b]thiophene

HRID 649007Notes

Reaction equation

HRID 649007 reaction equation
C([Li])CCC.CCOCC.Br[C:12]1[C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=2[S:15][CH:16]=1.Cl([F:26])(=O)(=O)=O>O>[F:26][C:12]1[C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=2[S:15][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 6150893-Bromo-7-methyl-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 147804953-Fluoro-7-methylbenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 ml of a 1.6M solution of butyllithium in abs. ether are added dropwise at -78° to a solution of 18.1 g of 3-bromo-7-methylbenzo[b]thiophene in abs. ether. After 20 Minutes 9 g of perchlorylfluoride are introduced under inert gas and with stirring whereby the reaction temperature is maintained below -60°. The resulting mixture is stirred for 30 minutes at -78° and then slowly warmed to 0°, mixed with water and the organic phase separated, washed, dried and concentrated under vacuum. The residue is chromatographed over silica gel (eluant: hexane) to obtain the title compound as an oil.

Workup

  1. temperatureis maintained below -60°
  2. stirringThe resulting mixture is stirred for 30 minutes at -78°
  3. temperatureslowly warmed to 0°
  4. customthe organic phase separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe residue is chromatographed over silica gel (eluant: hexane)

Sources & evidence

ORD record
ord-ab3cba378ab74919a0b7488bb7a5ee89
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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