Sodium Bicarbonate → HCID 13225968, compound

2-bromo-3-bromomethyl benzofuran prepared from Step A (7.67 g, 26.45 mmol) was immediately dissolved in dioxane (30 mL), followed by a solution of NaHCO3 (2.67 g, 1.2 eq.) in water (30 mL). The mixture was refluxed for 1 h with vigorous stirring, cooled to room temperature, diluted with water (150 mL) and extracted with dichloromethane (5×100 mL). The extract was washed with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The resulting orange oil was dissolved in chloroform (12 mL) and left to stand at −20° C. The resulting yellow prisms were filtered at −40° C., washed with chloroform, and filtered cold. Yield: 3.72 g (62%). MS (m/e): 228, 226 (M+), 211, 209, 183, 181, 171, 169, 147, 118, 102, 91. 1H-NMR (acetone-D6): 4.29 (t, 1H, J=6 Hz) 4.73 (d, 2H, J=6 Hz) 7.32 (m, 2H) 7.51 (d, 1H, J=8 Hz) 7.78 (dd, 1H, J=8 Hz, 2 Hz). 13C-NMR (acetone-D6): 54.74, 110.64, 119.96, 123.28, 124.57, 126.51, 128.12, 155.37.

1. temperatureThe mixture was refluxed for 1 h with vigorous stirring
2. extractionextracted with dichloromethane (5×100 mL)
3. washThe extract was washed with brine
4. dry with materialdried over sodium sulfate
5. customthe solvent removed under reduced pressure
6. dissolutionThe resulting orange oil was dissolved in chloroform (12 mL)
7. waitleft
8. customto stand at −20° C
9. filtrationThe resulting yellow prisms were filtered at −40° C.
10. washwashed with chloroform
11. filtrationfiltered cold

ORD record

ord-4ea146ff678d4503b81dfc10b9d235df

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114382B2