Water → HCID 59643026, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-Isopropyl-3-methoxy-2-methoxymethoxy-benzoate in 5 mL dry CH2Cl2 cooled to −80° C., BBr3 (3.4 mL of a 1 m solution in CH2Cl2) was added dropwise via a syringe. The mixture was then stirred 30 min. at −70° C., then the cooling bath was removed and the stirring continued at r.t. for 1 h. The reaction was the quenched by addition of H2O and the resulting mixture was extracted twice with 30 mL CH2Cl2. The combined organic fractions were dried over MgSO4 and evaporated in vacuo to yield a brown solid. This material was redissolved in 1 mL AcOH to which 2.5 mL HBr (33% in AcOH) was added The mixture was stirred at 120° C. for 5 h, then H2O was slowly added and the mixture was extracted with EtOAc. The organic layer was washed twice with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo to yield the desired product as a brown solid.

Provenance & Evidence