Tributyltin Chloride → HCID 60007617, compound

HRID 410008Notes

Reaction equation

HRID 410008 reaction equation
[Li]CCCC.[S:6]1[C:10]2[C:11]3[S:16][CH:15]=[CH:14][C:12]=3[S:13][C:9]=2[CH:8]=[CH:7]1.[Sn:17](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21]>>[CH2:26]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[C:15]1[S:16][C:11]2[C:10]3[S:6][CH:7]=[CH:8][C:9]=3[S:13][C:12]=2[CH:14]=1)[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 3

HCID 15096Tributyltin ChlorideHCID 137985Dithieno(3,2-b:2',3'-d)thiopheneHCID 178418339Butyllithium

Product 1

HCID 60007617HCID 60007617, compound

Procedure

2.5 M of n-BuLi (2.04 mL/hexane, 5.09 mmol) was added to dithieno[3,2-b;2′,3′-d]thiophene 20 (1 g, 5.09 mmol/THF (20 mL)) and reacted at 0° C. for 1 hour under a dry and anaerobic operation condition to form a solution. SnBu3Cl (1.58 mL, 5.6 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 (25, 2.1 g, 85%).

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 (25, 2.1 g, 85%)

Sources & evidence

ORD record
ord-f7dfc3658fa142289c60e0ef87d5964f
Source dataset
uspto-grants-2014_06
Patent number
US08759543B2

Reaction notes

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