Triethylamine → 2-Bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzene

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Bromo-4-tert-butylphenol	HCID 75147	—
Reactant	1-(Chloromethoxy)-2-methoxyethane	HCID 77590	—
Reactant	8-bromo-3,6-di-tert-butyl-3,4-dihydro-2H-benzo[e][1,3]oxazine	HCID 86718559	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-Bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzene	HCID 86718561	72.3%

Reaction Steps

To a solution of 2-bromo-4-(tert-butyl)phenol [Intermediate 1, Step 1] (5.0 g, 21.8 mmol) and triethylamine (4.4 g, 43.5 mmol) in anhydrous dichloromethane (20 mL) at room temperature under nitrogen was added dropwise 2-methoxyethoxymethyl chloride (2.5 mL, 21.9 mmol) and the reaction mixture stirred overnight. The reaction mixture was poured into water (100 mL), the organic phase separated, dried (MgSO4), filtered and concentrated under reduced pressure to give 2-bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzene (5.0 g, 72% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08962657B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-2105ec3caf6b4c2d840749d53e4e87fc
Source note	uspto-grants-2015_02