Ethyl Acetate → tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)-3-(4-bromophenyl)propan-2-yl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	N-bromobutanimide	HCID 67184	—
Reactant	tert-Butyl(1-(4-bromophenyl)-3-((2-(hydroxymethyl)benzyl)oxy)propan-2-yl)carbamate	HCID 123944090	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)-3-(4-bromophenyl)propan-2-yl)carbamate	HCID 123844053	50%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of compound 3h (4.15 g, 9.2 mmol) in dry THF (50 mL) was added NBS (4.1 g, 23 mmol) and PPh3 (6 g, 23 mmol) at 0° C. The mixture was stirred at 0° C. for 20 min. Then the mixture was stirred at rt for 2 hr. The solvent was evaporated in vacuo and purified by CC eluting with PE:EA=4:1 to give 3i as a white solid (2.3 g, 50% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08940722B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-67bd00b7885d4893a4db9754282a1d4d
Source note	uspto-grants-2015_01