1-Bromo-4-fluorobenzene → Stannane, (4-fluorophenyl)trimethyl-

HRID 1736298Notes

Reaction equation

HRID 1736298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][Sn:15](Cl)([CH3:17])[CH3:16]>C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([Sn:15]([CH3:17])([CH3:16])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

Product 1

HCID 618619Stannane, (4-fluorophenyl)trimethyl-Yield 28.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.0 g (13 mmol) of 4-fluorobromobenzene, 100 ml of anhydrous diethyl ether, 12 ml (19 mmol) of 1.6 M n-butyllithium (hexane solution) and 3.8 g (19 mmol) of trimethyltin chloride were subjected to reaction, treatment and purification in the same manner as in Example 13 (a) to give 970 mg of 4-flurophenyltrimethyltin as a colorless oil (yield 22%).

Sources & evidence

ORD record
ord-09b803c6dd774a7d87401f36e6ea935c
Source dataset
uspto-grants-1996_07
Patent number
US05541169

Reaction notes

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