Sodium Sulfate → HCID 56924484, compound

To a solution of 5-chloro-1,2-difluoro-3-nitrobenzene (1.62 g, 8.4 mmol) in acetic acid (30 mL) was added tin(II) dichloride dihydrate (11.4 g, 50.4 mmol). The mixture was stirred for 1.25 h at rt, and then the acetic acid was removed in vacuo. The residue was transferred to a 500-mL Erlenmeyer flask in a minimal amount of ethyl acetate. The resulting suspension was then diluted with approximately 200 mL of ether, and then the flask was placed into an ice bath. To the vigorously stirring mixture was added 50% aqueous sodium hydroxide (10 mL), and a pale yellow solid formed. Celite and sodium sulfate were added to adsorb and dry the precipitate. All the solids were removed by filtration, rinsed with ethyl acetate, and discarded. The filtrate was concentrated, and the residue was purified by flash chromatography (80% hexanes:20% ethyl acetate). The desired 5-chloro-2,3-difluoroaniline was isolated as an orange oil (913 mg, 5.6 mmol, 66% yield). 1H NMR (400 MHz, CDCl3): 6.57-6.52 (m, 2H), 3.91 (br s, 2H); GCMS for C6H4ClF2N: 163 (M+).

1. customthe acetic acid was removed in vacuo
2. additionThe resulting suspension was then diluted with approximately 200 mL of ether
3. customthe flask was placed into an ice bath
4. stirringTo the vigorously stirring mixture
5. additionwas added 50% aqueous sodium hydroxide (10 mL)
6. customa pale yellow solid formed
7. customdry the precipitate
8. customAll the solids were removed by filtration
9. washrinsed with ethyl acetate
10. concentrationThe filtrate was concentrated
11. customthe residue was purified by flash chromatography (80% hexanes:20% ethyl acetate)

ORD record

ord-d37a6edc6af5475d898d39f88dabd90c

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846959B2