Potassium Carbonate → (5-Chloro-2,3-dihydrobenzofuran-2-yl)methanol

Temperature

50 °C

To a solution of 4-chloro-2-(prop-2-en-1-yl)phenol (17 g, crude, nominally 101 mmol) in chloroform (100 ml) was added mCPBA (17.4 g, 101 mmol, 1 eq) with stirring for 1 h at 50° C. in an oil bath. Then the reaction mixture was concentrated under vacuum and re-dissolved in MeOH (100 ml). Potassium carbonate (27.6 g, 200 mmol, 2 eq) was added and the mixture was stirred for 5 hours at 50° C. The solids were filtered off and the filtrate was concentrated under vacuum. The crude material was purified by silica gel chromatography using 3% ethyl acetate in petroleum ether to elute. The product-containing fractions were combined and concentrated under vacuum to afford (5-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol as yellow oil (6.15 g); 1H NMR (300 MHz, CDCl3): δ 7.00-7.18 (m, 2H), 6.80 (d, J=8.7 Hz, 1H), 4.88-4.97 (m, 1H), 3.85-3.90 (m, 1H), 3.70-3.79 (m, 1H), 3.19-3.27 (dd, J=9.3 Hz, 15.9 Hz, 1H), 2.98-3.05 (dd, J=7.5 Hz, 15.9 Hz, 1H), 2.10 (broad s, 1H).

1. concentrationThen the reaction mixture was concentrated under vacuum
2. dissolutionre-dissolved in MeOH (100 ml)
3. stirringthe mixture was stirred for 5 hours at 50° C
4. filtrationThe solids were filtered off
5. concentrationthe filtrate was concentrated under vacuum
6. customThe crude material was purified by silica gel chromatography
7. washto elute
8. concentrationconcentrated under vacuum

ORD record

ord-c5fd025394a84d038e438962e14a0072

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249102B2