1,3-Dichloro-2-isocyanatobenzene → Methyl 3,5-dibromo-4-[({[(2,6-dichlorophenyl)amino]carbonyl}oxy)methyl]benzoate

Participants

Reaction Steps

To a stirred solution of methyl 3,5-dibromo-4-(hydroxymethyl)benzoate (11 g, 34 mmol, 1 eq) in CH2Cl2 (50 mL) was added 2,6-dichlorophenylisocyanate (7 g, 37.2 mmol, 1.1 eq) and 4-N,N-dimethylaminopyridine (few crystals). Stirred at rt. After 15 min, the flask was thick with precipitate. Added 50 L CH2Cl2 to facilitate stirring and let stir overnight. Removed the CH2Cl2 under reduced pressure. Triturated the residue with Et2O and collected the solids giving methyl 3,5-dibromo-4-[({[(2,6-dichlorophenyl)amino]carbonyl}oxy)methyl]benzoate.

Provenance & Evidence