Synthesis
To a solution of 2,6-dibromophenol (58.0 g, 230.2 mmol) in THF (300 mL) at 0 ˚C was added NaH (13.8 g, 60% dispersion in mineral oil). After 5 min of stirring at 0 ˚C, MOMCl (22.5 mL, 300 mmol) was added via a syringe. The reaction mixture was then allowed to slowly warm to 25 ˚C, and following 2 h of additional stirring at that temperature the reaction mixture was poured into Et2O (300 mL) and washed extensively with 3 M NaOH (3 × 75 mL) to remove any residual phenol starting material. The organic layer was then dried (MgSO4) and concentrated to give MOM-protected 2,6-dibromophenol (66.2 g, 97%) as a yellow oil. Reference: Nicolaou, K. C.; Snyder, S. A.; Huang, X.; Simonsen, K. B.; Koumbis, A. E.; Bigot, A. J. Am. Chem. Soc. 2004, 126, 10162−10173.
Uses
1,3-Dibromo-2-(methoxymethoxy)benzene is an intermediate in the synthesis of 3-[4-(2-Pyridylsulfamoyl)phenyl] Sulfasalazine (P995810), an impurity of Sulfasalazine (S699084). Sulfasalazine is an anti-inflammatory agent (gastrointestinal). Sulfasalazine has been used in granulomatous colitis.
