Acetamide → N-(3-bromo-5-fluorophenyl)acetamide

HRID 2098072Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([NH2:10])(=[O:9])[CH3:8].[Br:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14](Br)[CH:13]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:11][C:12]1[CH:13]=[C:14]([NH:10][C:7](=[O:9])[CH3:8])[CH:15]=[C:16]([F:18])[CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of tris(dibenzylideneacetone)dipalladium (0.20 g, 0.22 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene (0.13, 0.22 mmol) and cesium carbonate (5.0 g, 15.41 mmol) under N2 gas was added acetamide (0.90, 14.73 mmol), 1,3-dibromo-5-fluorobenzene (2.8 g, 10.83 mmol) and dioxane (22 mL). The reaction mixture was heated at 80° C. overnight and concentrated under reduced pressure. Purification by flash chromatography (silica, 50:50 ethyl acetate/hexane) gave N-(3-bromo-5-fluorophenyl)acetamide (3.51 g, quantitative). Retention time (min)=1.945, method [4], MS (ESI) 232.0 (M+H).

Workup

concentrationconcentrated under reduced pressure
customPurification by flash chromatography (silica, 50:50 ethyl acetate/hexane)

Sources & evidence

ORD record: ord-407329f572e64dceb81f29afa4c5d8ae
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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