2,2-Difluoro-5-formylbenzodioxole → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Temperature

0 °C

A cooled (0° C.) solution of commercially available 2,2-difluorobenzo[d][1,3]dioxole-5-carbaldehyde (1.500 g; 8.06 mmol) in anh. MeOH (60 ml) was treated portionwise with NaBH4 (1.524 g; 40.29 mmol), and the resulting mixture was stirred at 0° C., under nitrogen, for 1 h. After concentration to dryness under reduced pressure, the resulting residue was treated with water (30 ml), and extracted with DCM (2×100 ml). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, concentrated to dryness under reduced pressure, and the residue was further dried under HV affording (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol as a colorless oil. LC-MS (conditions D): tR=0.85 min.; no ionisation.

1. concentrationAfter concentration to dryness under reduced pressure
2. additionthe resulting residue was treated with water (30 ml)
3. extractionextracted with DCM (2×100 ml)
4. washThe mixed organic layers were washed with brine
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure
8. customthe residue was further dried under HV

ORD record

ord-432e3b9acde04b99af151ba54ac822ce

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242970B2