Water → HCID 11493226, compound
Reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:27])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22]OC)=[CH:18][CH:17]=[C:16]([C:25]#[N:26])[CH:15]=2.B(Br)(Br)Br.O.C(OCC)(=O)C>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:27])[O:13][C:14]2[C:19]([C:20]=1[CH:21]=[CH2:22])=[CH:18][CH:17]=[C:16]([C:25]#[N:26])[CH:15]=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
3-(2,4-Dimethoxy-phenyl)-4-(2-methoxy-ethyl)-2-oxo-2H-chromene-7-carbonitrile (380 mg, 1.04 mmol) was dissolved in CH2Cl2 (12 mL) at room temperature in a 200 ml round bottom flask. The reaction mixture was then cooled to −30° C., and BBr3 (1.8 ml) was added, then the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was cooled to 0° C. and water (40 mL) was added, followed by ethyl acetate (50 mL). The reaction mixture was then poured into a separation funnel. The organic layer separated and washed with water (1×40 ml) and brine (1×30 ml). The organic layer was dried over sodium sulfate and concentrated. The product was purified on silica gel eluted with 50%-100% ethyl acetate in hexanes to yield the title compounds as a foam and a yellow solid, respectively.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- additionThe reaction mixture was then poured into a separation funnel
- customThe organic layer separated
- washwashed with water (1×40 ml) and brine (1×30 ml)
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
- customThe product was purified on silica gel
- washeluted with 50%-100% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-8415a11c8cdc4ea79566962b79a4d19d
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067619B2
Reaction notes
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