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温度

0 °C

A 1.24 g portion of 4,5-dichlorophthalic acid is dissolved in 40 mL anhydrous tetahydrofuran and the solution is cooled to 0° C. To this solution is slowly added 4 mL of borane-methyl sulfide. The reaction flask is first warmed to room temperature, then heated to reflux for 12 hours. The product mixture is cooled to 0° C., then slowly quenched with 50 mL methyl alcohol. Following removal of the solvent, the residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran. The organic layer is washed with 30 mL brine, then dried over magnesium sulfate. Purification by silica gel chromatography (2:1 ethyl acetate/hexane) affords 1.01 g of the desired product as a white solid, m.p. 128°-136° C.

1. temperatureThe reaction flask is first warmed to room temperature
2. temperatureheated
3. temperatureto reflux for 12 hours
4. temperatureThe product mixture is cooled to 0° C.
5. customslowly quenched with 50 mL methyl alcohol
6. customremoval of the solvent
7. customthe residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran
8. washThe organic layer is washed with 30 mL brine
9. dry with materialdried over magnesium sulfate
10. customPurification by silica gel chromatography (2:1 ethyl acetate/hexane)