4-Bromobiphenyl → ([1,1'-Biphenyl]-4-yl)(tributyl)stannane

HRID 410005Notes

Reaction equation

HRID 410005 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[Sn:19](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23]>>[CH2:28]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 3

HCID 71014-BromobiphenylHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 57334235([1,1'-Biphenyl]-4-yl)(tributyl)stannane

Procedure

2.5 M of n-BuLi (2.1 mL/hexane, 5.32 mmol) was added to 4-bromobiphenyl (1.24 g, 5.32 mmol/THF (20 mL)) and reacted at −78° C. for 40 minutes under a dry and anaerobic operation condition to form a solution. SnBu3Cl (1.65 mL, 5.85 mmol) was then added to the solution and reacted at −78° C. for 1 hour. 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 colorless oily product (21, 1.83 g, 78%).

Workup

  1. customreacted at −78° C. for 40 minutes under
  2. customa dry
  3. customanaerobic operation condition to form a solution
  4. customreacted at −78° C. for 1 hour
  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 colorless oily product (21, 1.83 g, 78%)

Sources & evidence

ORD record
ord-000adc2683c1418aa85492f8cfdf5de8
Source dataset
uspto-grants-2014_06
Patent number
US08759543B2

Reaction notes

Loading…