Isopropanol → 1-Chloro-4-fluoro-5-nitro-2-(propan-2-yloxy)benzene

A mixture of 2-chloro-5-fluoro-4-nitrophenol (287 mg, 1.5 mmol), propan-2-ol (90 mg, 1.5 mmol), diphenyl-2-pyridylphosphine (592 mg, 2.25 mmol) and di-tert-butyl azodicarboxylate (518 mg, 2.25 mmol) in tetrahydrofuran (10 ml) was stirred at room temperature under argon for 22 hrs. The mixture was treated with 1M HCl/diethyl ether (10 ml) and stirred at room temperature for 1 hr, then concentrated under vacuum and the residue dissolved in diethyl ether (10 ml), treated with 5M HCl acid (10 ml) and stirred for 30 mins. The organic layer was separated, washed with 5M HCl acid (10 ml), then 10% Na2CO3 solution (2×10 ml), dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with 5-70% ethyl acetate/60-80 petrol ether to afford the title compound as a yellow solid (153 mg, 43%).

1. stirringstirred at room temperature for 1 hr
2. concentrationconcentrated under vacuum
3. dissolutionthe residue dissolved in diethyl ether (10 ml)
4. additiontreated with 5M HCl acid (10 ml)
5. stirringstirred for 30 mins
6. customThe organic layer was separated
7. washwashed with 5M HCl acid (10 ml)
8. dry with material10% Na2CO3 solution (2×10 ml), dried (MgSO4)
9. concentrationconcentrated under vacuum
10. customThe residue was purified by chromatography on silica gel eluting with 5-70% ethyl acetate/60-80 petrol ether

ORD record

ord-e6a2c28da9a842fd920d3797328f7bb0

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288412B2