Tetrahydrofuran → HCID 18994287, compound

Temperature

20 °C

To a THF (15 mL) solution of 3-(p-nitrobenzenethioxy)bromobenzene (2.0 g, 6.4 mmol), prepared as in step 1, was added methanol (50 mL) and CuC1 (0.89 g, 99%, 9.0 mmol). The solution was cooled to ~10° C. in an icebath and solid potassium borohydride (1.13 g, 21 mmol) was added in small portions while maintaining the reaction temperature below 20° C. After complete addition of potassium borohydride the icebath was removed. The reaction was judged to be complete after 20 min and was quenched by adding water (40mL) while maintaining the reaction temperature under 20° C. The quenched reaction mixture was filtered through celite and partitioned between ether and water. After separating the layers the aqueous layer was extracted three times with ether. The combined organic layers were washed twice with brine and concentrated to 1/2 the original volume. The solution was treated with decolorizing carbon while drying over MgSO4, filtered through a celite pad, and concentrated in vacuo to give 3-(p-aminobenzenethioxy)bromobenzene (1.81 g, 101%) as a waxy red solid which was carried on without further purification.

1. additionwas added in small portions
2. temperaturewhile maintaining the reaction temperature below 20° C
3. customwas removed
4. customwas quenched
5. additionby adding water (40mL)
6. customThe quenched reaction mixture
7. filtrationwas filtered through celite
8. custompartitioned between ether and water
9. customAfter separating the layers the aqueous layer
10. extractionwas extracted three times with ether
11. washThe combined organic layers were washed twice with brine
12. concentrationconcentrated to 1/2 the original volume
13. additionThe solution was treated with decolorizing carbon
14. dry with materialwhile drying over MgSO4
15. filtrationfiltered through a celite pad
16. concentrationconcentrated in vacuo

ORD record

ord-255f009b829d4fae99f387206b6a8d55

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05516795