4-Bromoaniline → 4-Bromo-N,N-dibutylaniline

1-Bromobutane (41.1 g, 300 mmol), 4-bromoaniline (17.2 g, 100 mmol) and KOH (16.8 g, 300 mmol) were heated at reflux under nitrogen gas for about 18 hours. After cooling, the mixture was partitioned between water and hexane and the organic layer washed with water followed by brine. After drying over MgSO4 and filtering, the solvent was evaporated and the mixture distilled under reduced pressure. Distillate fractions collected between 25-100° C. and pressure of 360-210 mTorr contained a mixture of products and starting material. The fractions collected at 100-107° C. and 200 mTorr pressure afforded 12.1 g (43%) of pure product.

1. temperatureat reflux under nitrogen gas for about 18 hours
2. temperatureAfter cooling
3. customthe mixture was partitioned between water and hexane
4. washthe organic layer washed with water
5. dry with materialAfter drying over MgSO4
6. filtrationfiltering
7. customthe solvent was evaporated
8. distillationthe mixture distilled under reduced pressure
9. customcollected between 25-100° C.
10. additiona mixture of products
11. customThe fractions collected at 100-107° C.

ORD record

ord-4adb9100b7744788a05625d788d5a483

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586283B2