Butyl bromide → 4-Butoxyphenylacetonitrile

Temperature

80 °C

4-Hydroxybenzyl cyanide (5.0 g) and 1-bromobutane (5.7 g) were dissolved in dimethylformamide (100 mL), and potassium carbonate (6.2 g) was added to the resultant solution, followed by heating at 80° C. for one hour, to thereby allow reaction to proceed. After completion of reaction, the resultant reaction mixture was cooled, and then partitioned between brine and ethyl acetate. The resultant ethyl acetate layer was dried over anhydrous sodium sulfate, and concentrated. The thus-concentrated product was purified by use of a silica gel column employing hexane/ethyl acetate (4:1), to thereby produce 4-butoxybenzyl cyanide (5.1 g, yield: 70%). The thus-produced 4-butoxybenzyl cyanide (2.0 g) and the 4-methoxyethoxymethoxybenzaldehyde (2.2 g) produced in the production process for compound 1 were subjected to condensation in accordance with process A of (production process 2), to thereby yield an MEM form of the target product. Subsequently, the protective group was removed from the MEM form in accordance with (production process 3), to thereby produce the target product (0.7 g, yield: 23%).

1. customreaction
2. customAfter completion of reaction
3. customthe resultant reaction mixture
4. temperaturewas cooled
5. custompartitioned between brine and ethyl acetate
6. dry with materialThe resultant ethyl acetate layer was dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customThe thus-concentrated product was purified by use of a silica gel column

ORD record

ord-45c8567d635245f39c98fc81c525ea31

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07371773B2