Diisobutylaluminum hydride → 5-Bromo-4-methyl-1,3-dihydroisobenzofuran-1-ol

Temperature

-78 °C

To a solution of 5-bromo-4-methylisobenzofuran-1(3H)-one (3.45 g, 15.19 mmol) in toluene (100 mL) at −78° C. was added DIBAL-H (21.27 mL, 21.27 mmol) dropwise. After stirring at −78° C. for 2 h, the reaction was quenched by methanol at −78° C., then warmed to rt, then 20 mL of saturated sodium sulfate was added and the mixture was vigorously stirred at rt for 30 min. Next, the mixture was filtered and washed with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate, dried over sodium sulfate, then concentrated to give the title compound. LC/MS: (M−17)+: 210.92; 212.91.

1. customthe reaction was quenched by methanol at −78° C.
2. temperaturewarmed to rt
3. addition20 mL of saturated sodium sulfate was added
4. stirringthe mixture was vigorously stirred at rt for 30 min
5. filtrationNext, the mixture was filtered
6. washwashed with ethyl acetate
7. washThe filtrate was washed with saturated sodium bicarbonate
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-bcb895b43f324865a1e4f358bf7f00b2

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206198B2