2-Bromophenol → 1-Bromo-2-(2,2-diethoxyethoxy)benzene

Participants

Role	Name	HCID	Charge
Reactant	2-Bromophenol	HCID 7244	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	Ethane, 2-bromo-1,1-diethoxy-	HCID 74852	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Solvent	Diethyl Ether	HCID 3283	—
Product	1-Bromo-2-(2,2-diethoxyethoxy)benzene	HCID 22951432	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A solution of KOH pellets (85%, 0.68 g, 10.3 mmol) in water (1.5 mL) was added to 2-bromophenol (1 mL, 8.6 mmol). The mixture was diluted with DMSO (20 mL) and bromoacetaldehyde diethyl acetal (1.43 mL, 9.5 mmol) was added. The mixture was heated at 100° C. for 6 h, cooled to rt, diluted with ether (175 mL), washed with water (3×40 mL) and 5% aq NaOH (40 mL), and dried over MgSO4. Removal of the solvent left 1-(2,2-diethoxyethoxy)-2-bromobenzene (2.62 g, quant) as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07754737B2
Source dataset	uspto-grants-2010_07
ORD ID	ord-2413596cbc1b4467bf4a6cb999c51643
Source note	uspto-grants-2010_07