Triethylsilane → 4-Fluoro-7-methoxy-2,3-dihydrobenzo[b]thiophene

HRID 2220342Notes

Reaction equation

HRID 2220342 reaction equation
[F:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[F:1][C:2]1[C:7]2[CH2:8][CH2:9][S:10][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 221712354-Fluoro-7-methoxy-1-benzothiophene

Product 1

HCID 179819214-Fluoro-7-methoxy-2,3-dihydrobenzo[b]thiopheneYield 13%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-fluoro-7-methoxy-1-benzothiophene (1.55 g, 8.5 mmol, 1 eq) in trifluoroacetic acid (40 ml) was added triethylsilane (3.40 ml, 21.25 mmol, 2.5 eq). The mixture was heated to 60° C. for 48 hours, then cooled to room temperature and the solvent removed in vacuo. The crude product was purified by flash chromatography with a gradient of 40-60% chloroform in heptane to give 1.24 g, 80% recovered starting material and 199 mg, 13% yield of the title compound as a colourless oil: δH (300 MHz, CDCl3) 3.78-6.58 (2H, m, ArH), 3.82 (3H, s, CH3) and 3.44-3.30 (4H, m, SCH2CH2).

Workup

  1. temperaturecooled to room temperature
  2. customthe solvent removed in vacuo
  3. customThe crude product was purified by flash chromatography with a gradient of 40-60% chloroform in heptane
  4. customto give 1.24 g, 80%
  5. customrecovered

Sources & evidence

ORD record
ord-b0a97a2aa1ad4e9b9021bfac3e57239a
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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