1-Bromo-3-chloro-5-nitrobenzene → Tert-butyl 2-(3-chloro-5-nitrophenyl)acetate

Participants

Role	Name	HCID	Charge
Reactant	1-Bromo-3-chloro-5-nitrobenzene	HCID 17839838	—
Reactant	HCID 178451183	HCID 178451183	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Catalyst	Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene	HCID 129828017	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Tert-butyl 2-(3-chloro-5-nitrophenyl)acetate	HCID 69620897	82.2%

Reaction Steps

To a solution of 1-bromo-3-chloro-5-nitrobenzene 52.A (10.23 g, 43 mmol, available from Synchem Inc), Pd2(dba)3 (0.79 g, 0.87 mmol) and CTC-QPhos (1.20 g, 1.40 mmol) in THF (100 mL) was added 2-tert-Butoxy-2-oxoethylzinc chloride (95 mL, 0.5M solution in diethyl ether, 48 mmol, available from Rieke Metals). The mixture was stirred for 3 hours at room temperature. The reaction was then quenched by adding water (100 mL), washed with 1N HCl solution (2×100 mL), concentrated and purified by using flash chromatography on silica gel (0-10% AcOEt/Hexanes) to afford tert-butyl 2-(3-chloro-5-nitrophenyl)acetate 52.B (9.60 g, 82% yield) as a light pink oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08785468B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-e8cedd90e2014d4188d5094501243149
Source note	uspto-grants-2014_07