Acetone → 2806-12-4

A 3 L three neck round bottom flask equipped with a nitrogen inlet, a thermometer, an overhead stirrer and a solid addition funnel was charged with 250 mL acetic acid, 50 mL absolute ethanol and 29.5 g (0.27 mol) of 4-fluoroaniline. To this mixture was added acetone (23 mL, 6.31 mol) in one portion followed by the portion-wise addition of sodium acetate trihydrate over 5 min. This vigorously stirred mixture was cooled to 0° C. (dry-ice/acetone) and 4.5 g of sodium borohydride (1.2 mol) was added portion-wise via a solid addition funnel over 50 min while keeping the internal temperature below 10° C. During this addition, acetic acid (100 mL) and absolute ethanol (50 mL) were added to facilitate stirring. After the addition, the mixture was allowed to warm to room temperature, and then stirred at ambient temperature for 12 h. Sufficient ammonium hydroxide (30% aqueous) was added to adjust the pH to ˜8 while maintaining the internal temperature below 30° C. using an ice/water bath. The mixture was extracted with ether (4×400 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, then concentrated under reduced pressure to give the desired product as a black/brown oil (38 g).

1. additiona thermometer, an overhead stirrer and a solid addition funnel
2. additionwas added portion-wise
3. additionvia a solid addition funnel over 50 min
4. customthe internal temperature below 10° C
5. additionwere added
6. additionAfter the addition
7. stirringstirred at ambient temperature for 12 h
8. temperaturewhile maintaining the internal temperature below 30° C.
9. extractionThe mixture was extracted with ether (4×400 mL)
10. washThe combined organic layers were washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure

ORD record

ord-cd4a10ce452f4c8a850c0e0907e03e54

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06737383B1