Chloro(chloromethyl)[bis(4-fluorophenyl)]silane → [bis(4-Fluorophenyl)](1H-imidazol-1-ylmethyl)silane

HRID 371314Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(Cl)[CH2:9]Cl)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.[K].[H-].C([Al+]CC(C)C)C(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([SiH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 3.0 g (9.9 mmol) of bis(4-fluorophenyl)chlorochloromethylsilane and 50 mg of tetrabutylammonium hydrogen sulfate in 10 ml of toluene is added 2.2 g (20.5 mmol) of potassium imidazole. The resulting exotherm is controlled by cooling with ice-water. Th solution is heated at reflux for 5 hours and then was cooled to -70° C. A solution of 10.5 ml (10.5 mmol) of diisobutylaluminum hydride (1.0 molar) in tetrahydrofuran is then added dropwise, and the reaction is warmed to room temperature and quenched by dropwise addition of saturated aqueous ammonium chloride. The solution is diluted with methylene chloride and washed three times with water and once with brine. Drying over magnesium sulfate and removal of solvent gives a viscous oil which is triturated with ether to give the title compound.

Workup

temperatureTh solution is heated
temperatureat reflux for 5 hours
temperaturethe reaction is warmed to room temperature
customquenched by dropwise addition of saturated aqueous ammonium chloride
additionThe solution is diluted with methylene chloride
washwashed three times with water
dry with materialDrying over magnesium sulfate and removal of solvent
customgives a viscous oil which
customis triturated with ether

Sources & evidence

ORD record: ord-d0061b22668941c1829a4bfb896d9772
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04530922

Reaction notes

Loading…