Sodium Hydroxide → HCID 58764125, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	(Trifluoromethyl)trimethylsilane	HCID 552549	—
Reactant	1-(Bromomethyl)-2-methoxy-3-methylbenzene	HCID 14433798	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 58764125	HCID 58764125	90.4%

Reaction Conditions

Temperature	55 °C

Reaction Steps

Trimethyl(trifluoromethyl)silane (25.39 mL, 162.5 mmol) was added to a stirred mixture of 1-bromomethyl-2-methoxy-3-methyl-benzene(19 g, 65 mmol), KF (9.44 g, 162.5 mmol), CuI (37.10 g, 195 mmol) in DMF (75 mL) and NMP (75 mL). The reaction mixture was heated to 55° C. under N2 for 15 hours. The mixture was poured into water, made basic with 1 N NaOH and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a black oil. Flash column chromatography (0% to 60% EtOAc in hexanes) gave the product as a yellow oil (12.0 g). LCMS: APCI−VE=203

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07151105B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-1216d8545290425b98d479d6ca277827
Source note	uspto-grants-2006_12