2,2-Dibromopropane → HCID 21251132, compound

Temperature

20 °C

A solution of 3-chloro-4-dimethylcarbamoylthiophenyl acetic acid methyl ester (10.028 grams; 34.848 mmol) in dry MeOH (90 mL) was treated with a solution of sodium methoxide (4.37 M; 11.16 mL; 48.788 mmol). The reaction was refluxed for 2 hours. The reaction mixture was cooled to 20 ° C. and transferred to a dropping funnel. The dropping funnel was placed atop a flask containing a solution of dibromopropane (14.15 mL; 139.392 mmol) in dry MeOH (50 mL). The contents of the dropping funnel were added to the flask dropwise, and the solution stirred for 2 hours. The reaction mixture was partitioned between isopropyl acetate and pH 4 buffer. The layers were separated and the organic washed once with water. The organic was dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography afforded 3-chloro-4-(3-bromopropyl)thiophenyl acetic acid methyl ester.

1. temperatureThe reaction was refluxed for 2 hours
2. customtransferred to a dropping funnel
3. customThe dropping funnel was placed atop a flask
4. additionThe contents of the dropping funnel were added to the flask dropwise
5. customThe reaction mixture was partitioned between isopropyl acetate and pH 4 buffer
6. customThe layers were separated
7. washthe organic washed once with water
8. dry with materialThe organic was dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-2955abd08e204ba9b132028855d0f81b

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090836