Butyl bromide → HCID 86757156, compound

Temperature

-78 °C

To a stirred solution of 2.0 g (9.99 mmol) trans-2-butene-1,4-dicarboxylic acid diethyl ester in 80 ml THF was added 2.54 g (59.9 mmol) anhydrous lithium chloride and the resulting suspension cooled to −78° C. 10.0 ml (20.0 mmol) of a 2 M solution of LDA in THF was added dropwise and stirring continued for 45 min. 2.2 ml (20.4 mmol) butyl bromide was then added and stirring continued for 15 min at −78° C., then 30 min at 0° C, and then 4 h at room temperature. The reaction was quenched by addition of saturated ammonium chloride solution and the mixture extracted three times with ether. The combined organic phases were washed successively with saturated ammonium chloride solution, water, and saturated brine, dried over sodium sulphate, and concentrated in vacuo. Successive flash chromatography (10% EtOAc in hexane for first column; then gradient: 10-100% toluene in cyclohexane for second column) afforded 509 mg (16%) of the title compound as a yellow oil. MS m/e (%): 330 ([M+NH4]+, 100).

1. stirringstirring
2. waitcontinued for 15 min at −78° C.
3. custom30 min
4. customat 0° C
5. custom4 h
6. customat room temperature
7. customThe reaction was quenched by addition of saturated ammonium chloride solution
8. extractionthe mixture extracted three times with ether
9. washThe combined organic phases were washed successively with saturated ammonium chloride solution, water, and saturated brine
10. dry with materialdried over sodium sulphate
11. concentrationconcentrated in vacuo

ORD record

ord-61edc558559642a89cc81781f6cc1cae

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262089B1