Hydrochloric Acid → 3-fluoro-N-methylaniline

1-((3-Fluoroanilino)methyl)-1H-benzotriazole (173.9 g) was slurried in dry tetrahydrofuran. Sodium borohydride (32.5 g) was added portionwise to the mixture at room temperature. After addition was complete, the mixture was heated at reflux for 4 hours. The solution was cooled and poured slowly into 400 mL of 5 M hydrochloric acid with ice and stirred for 1 hour at room temperature. The solution pH was adjusted to 9-10 using 10 M sodium hydroxide solution. The product was extracted using diethyl ether. The ether extracts were washed successively with 1 M sodium hydroxide solution, saturated sodium chloride solution, and water. The organic phase was dried over sodium sulfate and evaporated under reduced pressure to yield 87.5 g (97%) of 3-fluoro-N-methylaniline as a colorless oil. [NMR (200 MHz, DMSO-d6): δ 2.76 (s, 3H); 3.41 (br s, 1H); 6.59-6.92 (m, 3H); 7.27 (q, J=8.0 Hz, 1H)].

1. additionAfter addition
2. temperaturethe mixture was heated
3. temperatureat reflux for 4 hours
4. temperatureThe solution was cooled
5. extractionThe product was extracted
6. washThe ether extracts were washed successively with 1 M sodium hydroxide solution, saturated sodium chloride solution, and water
7. dry with materialThe organic phase was dried over sodium sulfate
8. customevaporated under reduced pressure

ORD record

ord-3b404c1921804e6298ec4573f000a872

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296707B2