2-Bromonaphthalene → Stannane, trimethyl-1-naphthalenyl-

HRID 743723Notes

Reaction equation

HRID 743723 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[CH3:17][Sn:18](Cl)([CH3:20])[CH3:19].O1CCOCC1.[NH4+].[OH-]>C(OCC)C>[C:8]1([Sn:18]([CH3:20])([CH3:19])[CH3:17])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:7]=1

Participants

7

Reactant 5

HCID 113722-BromonaphthaleneHCID 14016Trimethyltin chlorideHCID 14923Ammonium HydroxideHCID 312751,4-DioxaneHCID 178418306HCID 178418306, compound

Product 1

HCID 136760Stannane, trimethyl-1-naphthalenyl-Yield 95.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

tert-Butyllithium (12.5 ml, 21.25 mmol, 1.7M in pentane) is added dropwise to a stirred solution of 2-bromonaphthalene (2 g, 9.66 mmol) in anhydrous diethyl ether (40 ml) under argon at -78° C. The solution is stirred for 15 min and then treated with a 2.71M solution of trimethyltin chloride in dioxane (4.63 ml, 12.55 mmol). The heterogeneous mixture is warmed to room temperature, diluted with diethyl ether (150 ml) and treated with 10% NH4OH solution (90 ml) for 5 minutes. The two phases are separated and the organic phase is washed with water followed by brine, dried over MgSO4 and concentrated to dryness. The oil is purified by flash silica chromatography (hexane) to give napthyltrimethyl stannane (2.69 g, 95.6%).

Workup

  1. customThe two phases are separated
  2. washthe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe oil is purified by flash silica chromatography (hexane)

Sources & evidence

ORD record
ord-0f24611306cf4170b3ec0fe91a9295fc
Source dataset
uspto-grants-1996_09
Patent number
US05556990

Reaction notes

Loading…