Water → (5-Amino-2-chlorophenyl)methanol

To a solution of (2-chloro-5-nitrophenyl)methanol (5.00 g, 26.7 mmol) in EtOAc (100 mL) was added water (2.41 mL, 134 mmol) followed by tin(II) chloride (12.7 g, 67.0 mmol). The solution was stirred at RT for 21 h, then additional tin(II) chloride (5.06 g, 26.7 mmol) was added, and the mixture heated at 50° C. for 2 h, and then at 70° C. for 3 h. The cooled mixture was slowly basified with 1N sodium hydroxide solution (˜300 mL). The suspension was filtered through Celite, washing with EtOAc. The aqueous layer was extracted with EtOAc (3×100 mL), then the combined organics washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (3.92 g, 93%). LCMS (Method 3): Rt 0.98 min, m/z 158 [MH+].

1. temperaturethe mixture heated at 50° C. for 2 h
2. waitat 70° C. for 3 h
3. filtrationThe suspension was filtered through Celite
4. washwashing with EtOAc
5. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
6. washthe combined organics washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-b4aa56a2079b4334bd2803754fa93d2e

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440974B2