Triethylamine → 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Borate	HCID 26574	—
Reactant	4-Bromo-2-methoxyphenol	HCID 262234	—
Reactant	2,4-Dimethoxypyrimidine-5-boronic acid pinacol ester	HCID 16218388	—
Reactant	1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4(1H,3H)-pyrimidinedione	HCID 16414225	—
Reactant	3,4-Dimethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde	HCID 21923914	—
Product	2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol	HCID 2734650	—

Reaction Steps

Solution 1 was transferred under N2 to a pressure-equalising dropping funnel and added to Solution 2 over 6 h. Stirred at RT overnight before heating at 40–50° C. for ˜8 h. After stirring overnight at RT a white ppt had formed. NEt3 (149 ml; 1.07 mol) was added followed by slow addition of 2-methoxy-4-bromophenol (91.6 g; 0.451 mol). Finally, the activated catalyst (Solution 3) was added and the resultant dark brown solution was stirred at 100° C. GC analysis after 20 hours showed the desired borate compound at 11.1 minutes (62%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07122694B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-d0b69ae212414818a1ccfb7f1bea81c8
Source note	uspto-grants-2006_10