Ethyl Acetate → 2-Bromo-4-fluorobenzaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	N-Methylmorpholine N-oxide monohydrate	HCID 2724197	—
Reactant	2-Bromo-1-(bromomethyl)-4-fluorobenzene	HCID 10706977	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Bromo-4-fluorobenzaldehyde	HCID 2773319	98.5%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of the benzyl bromide of Step 1 (59 g, 220 mmol) in dioxane (500 mL) at r.t. was added N-methylmorpholine N-oxide monohydrate (89 g, 660 mmol). The reaction mixture was stirred for 1 hour at 70° C. and poured into a mixture of saturated aqueous NH4Cl and EtOAc. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4 and concentrated to give 44 g of the title compound as a white solid and used as such.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07144913B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-6ec8e74b329d4168af8ab1e906afc5a9
Source note	uspto-grants-2006_12