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

HRID 2111767Notes

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-5a3b10c4f09d4068a97862a6e31e76d4
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521450B2

Reaction notes

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