Diethyl Ether → 4,5-Bis(chlorodimethylsilyl)-2,7-di(tert-butyl)-9,9-dimethylxanthene

Participants

Role	Name	HCID	Charge
Reactant	Diethyl Ether	HCID 3283	—
Reactant	Dichlorodimethylsilane	HCID 6398	—
Reactant	4,5-Dibromo-2,7-bis(1,1-dimethylethyl)-9,9-dimethyl-9H-xanthene	HCID 4221248	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Hexane	HCID 8058	—
Product	4,5-Bis(chlorodimethylsilyl)-2,7-di(tert-butyl)-9,9-dimethylxanthene	HCID 67069050	—

Reaction Conditions

Temperature	-65 °C

Reaction Steps

The reaction outlined in the reaction scheme below is as follows: Et2O (125 mL) and 4,5-dibromo-2,7-di(tert-butyl)-9,9-dimethylxanthene (9.54 g, 19.9 mmol) were combined and cooled to −65° C. A hexane solution of BuLi (19.2 mL, 47.7 mmol) was added dropwise over 5 min and the colorless suspension was allowed to warm to −30° C. over a period of 45 min during which time the starting material dissolved (at about −40° C.). After 15 min at −30° C. the solution was cooled to −80° C. and cold SiMe2Cl2 (20.5 g, 159 mmol) was added in one portion.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07910760B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-2483d4b7565d4f7b9bb5f328e901c76d
Source note	uspto-grants-2011_03