Di-tert-butyl dicarbonate → 4-Fluoro-3-(furan-2-yl)benzaldehyde

HRID 1837062Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].C([Sn](CCCC)(CCCC)[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)CCC.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CN(C=O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

3-Bromo-4-fluorobenzaldehyde (1 g, 4.93 mmol) in DMF (25 ml) was treated with 2-(tributylstannyl)furan (2.4 ml, 1.05 mmol), di-tert-butyl dicarbonate (1.75 g, 4.94 mmol), and tetrakis(triphenylphosphine)palladium (0) (570 mg, 0.4 mmol). The mixture was heated at 110° C. in a sealed high pressure tube over night, allowed to cool to ambient temperature, diluted with ethyl acetate, and washed with brine. The organic layer was further washed with 1N HCl, saturated NaHCO3, brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography using hexanes:diethyl ether (20:1) as eluent to provide the title compound as a pale yellow oil (0.96 g, 98%).

Workup

temperatureto cool to ambient temperature
washwashed with brine
washThe organic layer was further washed with 1N HCl, saturated NaHCO3, brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-63b0e8b33aaa4141aa4109b54123821f
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780872B2

Reaction notes

Loading…