Diisobutylaluminum hydride → 6-Bromo-1,3-dihydroisobenzofuran-1-ol

Temperature

-78 °C

Step 1) To a solution of 6-bromophthalide (144, 550 mg, 2.58 mmol) in dichloromethane (20.0 mL) was slowly added DIBAL-H (2.7 mL, 1.0M solution in hexane) at −78° C., and the reaction mixture was stirred for 1.5 h at −78° C. The resulting mixture was quenched with sat. Na2SO4 and allowed to warm to room temperature. To the mixture was added anhydrous Na2SO4, and the mixture was stirred for 12 h, then filtered and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide 6-bromo-1,3-dihydroisobenzofuran-1-ol (145, 530 mg, 96%) as yellow oil.

1. customat −78° C.
2. customThe resulting mixture was quenched with sat. Na2SO4
3. temperatureto warm to room temperature
4. additionTo the mixture was added anhydrous Na2SO4
5. stirringthe mixture was stirred for 12 h
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude was purified by silica gel column chromatography

ORD record

ord-5cd40f188d72430b94f3661e01c0cb50

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034921B2