p-Bromochlorobenzene → tributyl(4-chlorophenyl)stannane

HRID 964613Notes

Reaction equation

HRID 964613 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Li]CCCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>C1COCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 11112179tributyl(4-chlorophenyl)stannaneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromochlorobenzene (3.2 g, 16.62 mmol) was dissolved in dry THF (20 mL). After bringing the reaction temperature down to -78° C. with an acetone/dry ice bath, nBuLi (15.58 mL, 1.6M, 1.5 equiv.) was added slowly and stirred at -78° C. for 30 min. Tributyltinchloride (6.77 mL, 1.5 equiv.) was added and stirred overnight while bringing the reaction to room temperature. Reaction mixture was quenched by stirring the reaction flask open in air for 1 hour after which THF was rotavaporated off. Product was obtained as an oil (7.35g, 97%) after passing the mixture through a quick silica gel column eluting with 100% hexanes.

Workup

  1. customdown to -78° C.
  2. stirringstirred overnight
  3. customthe reaction to room temperature
  4. customReaction mixture
  5. customwas quenched
  6. stirringby stirring the reaction flask open in air for 1 hour after which THF

Sources & evidence

ORD record
ord-827165d6bcf648c69afc132f2c9fadb7
Source dataset
uspto-grants-1998_06
Patent number
US05770617

Reaction notes

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