Water → HCID 59643026, compound

Temperature

-70 °C

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.

1. customthe cooling bath was removed
2. waitthe stirring continued at r.t. for 1 h
3. customquenched by addition of H2O
4. extractionthe resulting mixture was extracted twice with 30 mL CH2Cl2
5. dry with materialThe combined organic fractions were dried over MgSO4
6. customevaporated in vacuo
7. customto yield a brown solid
8. additionwas added The mixture
9. stirringwas stirred at 120° C. for 5 h
10. extractionthe mixture was extracted with EtOAc
11. washThe organic layer was washed twice with saturated NaCl solution
12. dry with materialdried over MgSO4
13. customevaporated in vacuo

ORD record

ord-3c697cc4ae7d417fa5ffed3abf11cc5c

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07319101B2