Sulfuric Acid → tert-Butyl 2,4-dibromobutyrate

Participants

Reaction Conditions

Reaction Steps

2,4-Dibromobutanoic acid (the crude product from above) dissolved in DCM (10 L) in a 50 L-reactor. 2-Methylpropan-2-ol (12000 g, 162.16 mol) and boron anhydride (8000 g, 114.29 mol) were added to the above solution. 1680 g of H2SO4 was added dropwise to the above solution under N2 (gas) while maintaining the temperature at room temperature (25-30° C.). The mixture was allowed to react for 24 h at room temperature. Then 15 L aqueous Na2CO3 (sat.) was added to quench the reaction. The organic phase was separated and dried over Na2SO4. The solvent was removed under vacuum to give the crude product, which was purified by silica gel column chromatography to give tert-butyl 2,4-dibromobutanoate as a brown oil (3800 g, 12.58 mol, 39%).

Provenance & Evidence