m-Chloroperbenzoic acid → (5-Fluoro-2,3-dihydro-1-benzofuran-2-yl)methanol

Temperature

60 °C

Into a 500 ml round-bottomed flask that contained a solution of 2-allyl-4-fluoro-phenol (10.0 g, 65.7 mmol) in 300 ml of chloroform was added m-CPBA (11 g, 64 mmol, ˜0.96 eq). The mixture was heated at 60° C. (oil bath) for 6 hours. The contents were cooled to room temperature and the solids were filtered off and washed with 3×20 ml of chloroform The filtrate was washed with saturated aqueous NaHCO3 (2×100 mL) to remove traces of m-CPBA, dried over magnesium sulfate, filtered, and then concentrated under vacuum. The crude residue was then chromatographed on silica gel using petroleum ether/ethyl acetate to elute. The product-containing fractions were combined and concentrated under vacuum to afford 8.5 grams of the alcohol as a yellow oil (77%); 1H NMR (300 MHz, CDCl3): δ 6.91-6.88 (m, 1H), 6.84-6.78 (m, 1H), 6.72-6.68 (m, 1H), 4.99-4.90 (m, 1H), 3.90-3.85 (dd, J=3.3 Hz, 12 Hz, 1H), 3.78-3.70 (dd, J=3.3 Hz, 12 Hz, 1H), 3.29-3.21 (dd, J=9.3 Hz, 15.9 Hz, 1H), 3.01-3.08 (dd, J=7.5 Hz, 15.9 Hz, 1H).

1. customInto a 500 ml round-bottomed flask that contained
2. temperatureThe contents were cooled to room temperature
3. filtrationthe solids were filtered off
4. washwashed with 3×20 ml of chloroform The filtrate
5. washwas washed with saturated aqueous NaHCO3 (2×100 mL)
6. customto remove traces of m-CPBA
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customThe crude residue was then chromatographed on silica gel
11. washto elute
12. concentrationconcentrated under vacuum

ORD record

ord-66da29b8376146c184adb089725494fa

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249102B2