Hydrogen Bromide → 1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

HRID 1163050Notes

Reaction equation

C([O:8][C:9]1[C:10]([F:22])=[C:11]([CH2:18][C:19](=[O:21])[CH3:20])[C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)C1C=CC=CC=1.Br>C(OC(=O)C)(=O)C.C(O)(=O)C>[F:22][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[C:11]=1[CH2:18][C:19](=[O:21])[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

Method R-1: To a solution of 1-(3-benzyloxy-2-fluoro-6-nitrophenyl)-propan-2-one (3.03 g, 10 mmol) in acetic anhydride (5 mL) and acetic acid (5 mL) at room temperature was added hydrobromic acid (48% aqueous solution, 3 mL). After addition, the reaction was heated at 100° C. for 30 min and then cooled to room temperature. To this mixture was added 10 mL of hexanes with stirring. The solution was decanted and concentrated. The residue was diluted with ethyl acetate (50 mL) and washed with brine (3×20 mL). The organic layer was dried and concentrated in vacuo to provide 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (1.70 g, 80%) as a brown solid, which was used in the next step without further purification. LC/MS; (M+H)+=213.2

Workup

additionAfter addition
temperaturecooled to room temperature
customThe solution was decanted
concentrationconcentrated
additionThe residue was diluted with ethyl acetate (50 mL)
washwashed with brine (3×20 mL)
customThe organic layer was dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0938b8e4e47f492898ba2356a7e9c984
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820814B2

Reaction notes

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