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

HRID 984858Notes

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-fcd013e20a904f898be681a012d54bec
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869952B2

Reaction notes

Loading…