Einecs 211-027-4 → 1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

HRID 984854Notes

Reaction equation

[F:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:13][C:14](=[O:16])[CH3:15].[Cl-].[NH+]1C=CC=CC=1>Cl.C(OCC)(=O)C>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:13][C:14](=[O:16])[CH3:15]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one from previous step (454 mg, 21 mmol) and pyridinium chloride (0.9 g, 7.8 mmol) was stirred at 180° C. for 75 min. The reaction was cooled to room temperature, diluted with 1N HCl (3 mL) and ethyl acetate (10 mL) and filtered. The filtrate was washed with brine (2×), dried and concentrated in vacuo to give 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (410 mg, 96%) as a grey solid, which was used without further purification for the next step. LC/MS; (M+H)+=214. 1HNMR (CDCl3): δ 2.37 (s, 3H), 4.22 (s, 2H), 6.95 (dd, 1H), 7.95 (d, 1H, J=9.35 Hz).

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
washThe filtrate was washed with brine (2×)
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f0dc988e55364814b5c1302d07f021cc
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869952B2

Reaction notes

Loading…