Bromine → HCID 49766558, compound

Temperature

32.5 °C

To a stirred solution of 2-amino-5-nitro-phenol (500 g, 3.24 mol) in ACN (12 L) was added bromine (290 mL, 5.63 mol) drop wise over a period of 30 min. The mixture was stirred at 30-35° C. for 1 h, then the solvent was evaporated to dryness. Hexane (2 L) was added and the mixture evaporated to dryness. Hexane (5 L) was added and the mixture stirred for 1 h and filtered. The solid (1102 g) was washed with hexane (2 L). The residue was added to ice-cold H2O (2.5 L) followed by the addition of a saturated solution of sodium thiosulfate (2.5 L) and extraction with EtOAc (2×10 L). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated at 40-45° C. in vacuo to obtain i (643 g, 85%).

1. customthe solvent was evaporated to dryness
2. additionHexane (2 L) was added
3. customthe mixture evaporated to dryness
4. additionHexane (5 L) was added
5. stirringthe mixture stirred for 1 h
6. filtrationfiltered
7. washThe solid (1102 g) was washed with hexane (2 L)
8. additionThe residue was added to ice-cold H2O (2.5 L)
9. additionfollowed by the addition of a saturated solution of sodium thiosulfate (2.5 L) and extraction with EtOAc (2×10 L)
10. washThe combined organic layers were washed with brine
11. dry with materialdried (Na2SO4)
12. filtrationfiltered
13. concentrationconcentrated at 40-45° C. in vacuo
14. customto obtain i (643 g, 85%)

ORD record

ord-f99a1a514a4941939c003d846e3433a0

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906902B2