Hydrochloric Acid → HCID 86674694, compound

Temperature

0 °C

In a 20 mL four-necked flask, 4-(difluoromethoxy)aniline (0.5 g, 3.14 mmol) and hydrochloric acid (37% in water, 0.54 ml, 6.6 mmol) were combined with water (5 ml) to give a light yellow solution. Cooled to 0° C. using an ice-bath, sodium nitrite (217 mg, 3.14 mmol) was dissolved in water (1 ml) and added carefully ensuring that the temperature did not increase above 5° C. Sodium azide (204 mg, 3.14 mmol) was dissolved in water (1 ml) and added drop-wise to the orange solution, keeping the temperature below 5° C. The reaction mixture was cooled at 0-5° C. for 1 hour and an orange emulsion was observed. The layers were separated using TBME and the organic layer was washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated under vacuum to yield 1-azido-4-(difluoromethoxy)benzene as an orange liquid.

1. customto give a light yellow solution
2. additionadded carefully
3. temperaturedid not increase above 5° C
4. additionadded drop-wise to the orange solution
5. customthe temperature below 5° C
6. temperatureThe reaction mixture was cooled at 0-5° C. for 1 hour
7. customThe layers were separated
8. washthe organic layer was washed with brine
9. dry with materialdried over sodium sulphate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-91051ada188b46b48247dbf12737bf8c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029370B2