Sodium Carbonate → 2-Nitro-4-(thiophen-2-yl)aniline

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Bromo-2-nitroaniline	HCID 70132	—
Reactant	2-Thiopheneboronic acid	HCID 2733960	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
Product	2-Nitro-4-(thiophen-2-yl)aniline	HCID 22664831	—

Reaction Conditions

Temperature	23 °C

Reaction Steps

4-Bromo-2-nitroaniline (1.0 eq) and Na2CO3 (2.0 eq) were dissolved in DMF/H2O (5:1) at room temperature. Nitrogen was bubbled through the reaction mixture for 5 minutes and PdCl2(dppf)2 (0.1 eq) was added. After stirring at 23° C. for approximately 10 minutes, 2-thiopeneboronic acid (1.1 eq) in DMF was added and the reaction was heated at 90° C. for 12 hours. After this time, the solution was concentrated and partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting black residue was purified by silica gel chromatography (0-20% EtOAc:hexanes) to yield an orange solid. LC/MS m/z 221.1 (MH+), Rf 2.67 minutes.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06605617B2
Source dataset	uspto-grants-2003_08
ORD ID	ord-00357f139b7f462783f596c395acc582
Source note	uspto-grants-2003_08