Water → 7-Fluorobenzo[d][1,3]dioxole-5-carbaldehyde

Temperature

60 °C

To a solution of 3-fluoro-4,5-dihydroxy-benzaldehyde (1.5 g, 9.6 mmol) and BrClCH2 (4.9 g, 38.5 mmol) in dry DMF (50 mL) was added Cs2CO3 (12.6 g, 39 mmol). The mixture was stirred at 60° C. overnight and was then poured into water. The resulting mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to afford 7-fluoro-benzo[1,3]dioxole-5-carbaldehyde (0.80 g, 49%). 1H NMR (300 MHz, CDCl3) δ 9.78 (d, J=0.9 Hz, 1H), 7.26 (dd, J=1.5, 9.3 Hz, 1H), 7.19 (d, J=1.2 Hz, 1H), 6.16 (s, 2H).

1. extractionThe resulting mixture was extracted with EtOAc (50 mL×3)
2. washThe combined organic layers were washed with brine (100 mL)
3. dry with materialdried over Na2SO4
4. customevaporated under reduced pressure
5. customto give the crude product, which
6. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1)

ORD record

ord-3e0dbafbfc9b4a70a449c8cff20d3bc4

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598181B2