Benzo(B)Thiophene → (1-Benzothiophen-2-yl)tributylstannane

HRID 410007Notes

Reaction equation

HRID 410007 reaction equation
[Li]CCCC.[S:6]1[CH:10]=[CH:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]1=2.[Sn:15](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>>[CH2:24]([Sn:15]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:20][CH2:21][CH2:22][CH3:23])[C:10]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 2735461(1-Benzothiophen-2-yl)tributylstannane

Procedure

2.5 M of n-BuLi (3.1 mL/hexane, 7.67 mmol) was added to benzo[b]thiophene (1.05 g, 7.67 mmol/THF (20 mL)) and reacted at 0° C. for 1 hour under a dry and anaerobic operation condition to form a solution. SnBu3Cl (2.38 mL, 8.44 mmol) was then added to the solution and reacted at 0° C. for 30 minutes. After returning to room temperature, the solution was continuously reacted for 8 hours. After the reaction was completed, the solution was extracted by ether (30 mL) and deionized water (50 mL). An organic phase was collected. After removal of ether by a rotary concentrator, the organic phase was purified by reduced-pressure distillation to form a transparent pale yellow oily product (23, 1.76 g, 54%).

Workup

  1. customreacted at 0° C. for 1 hour under
  2. customa dry
  3. customanaerobic operation condition to form a solution
  4. customreacted at 0° C. for 30 minutes
  5. customAfter returning to room temperature
  6. customthe solution was continuously reacted for 8 hours
  7. extractionthe solution was extracted by ether (30 mL) and deionized water (50 mL)
  8. customAn organic phase was collected
  9. customAfter removal of ether by a rotary concentrator
  10. distillationthe organic phase was purified by reduced-pressure distillation
  11. customto form a transparent pale yellow oily product (23, 1.76 g, 54%)

Sources & evidence

ORD record
ord-b0d69fd8543b4f6eaa7a1860333c0328
Source dataset
uspto-grants-2014_06
Patent number
US08759543B2

Reaction notes

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