3-(Bromomethyl)-5-fluoro-1-benzothiophene → 5-Fluoro-3-isobutyl-benzo[b]thiophene

HRID 1693137Notes

Reaction equation

HRID 1693137 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.[CH:13]([Mg]Br)([CH3:15])[CH3:14]>C1COCC1>[F:12][C:9]1[CH:10]=[CH:11][C:6]2[S:5][CH:4]=[C:3]([CH2:2][CH:13]([CH3:15])[CH3:14])[C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiopheneHCID 178418365HCID 178418365, compound

Product 1

HCID 597599805-Fluoro-3-isobutyl-benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-bromomethyl-5-fluorobenzothiophene (2.0 g; cf. Raga, Manuel; Palacin, Celia; Castello, Josep Maria; Ortiz, Jose A.; Cuberes, Maria Rosa; Moreno-Manas, Marcial, Eur. J. Med. Chem. (1986), 21(4), 329-32) in THF (30 ml) was added over 5 minutes isopropylmagnesium bromide (1.0 M, 16.6 ml). The reaction mixture was stirred at 50° C. for 5 h, cooled, quenched with ice/water and ammonium chloride solution, and extracted with ethyl acetate. The organic phases were washed with water, dried and concentrated. The residue was chromatographed on silica gel using heptane/methylene chloride as eluent to obtain the title compound (1.35 g) as a yellowish oil. MS (EI): 208.3 (M)

Workup

  1. temperaturecooled
  2. customquenched with ice/water and ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-251515dd99554df396bb60853627d78e
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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