1-Chloro-2-nitrobenzene → N-(4-Methoxyphenyl)-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (4.6 mg, 0.005 mmol, 1 mol % Pd), ligand 1 (see FIG. 1) (8.4 mg, 0.02 mmol) and NaOt-Bu (2 mg, 0.02 mmol) were stirred in 1 mL DME (anhy). After 10 minutes, the solution was added to a test tube containing (under an Argon atmosphere) K3PO4 (297 mg, 1.4 mmol), 2-nitrochlorobenzene (158 mg, 1.0 mmol), and p-anisidine (148 mg, 1.2 mmol). The test tube was capped and heated at 100° C. for 35 hours. The reaction mixture was cooled to r.t., diluted with ether and dodecane was added as an internal standard. The reaction mixture was purified by column chromatography (10% EtOAc/hexanes) to yield 238 mg (98% yield) of the product.

Provenance & Evidence