Benzene, 1-bromo-3-nitro- → HCID 86641451, compound

HRID 1189945Notes

Reaction equation

[CH2:1]([NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])[CH:2]=[CH2:3].Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1.CC(CC(OC(C)(C)C)=O)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:7][C:6]([F:9])([F:8])[C:5]([NH:4][CH2:1][CH:2]=[CH:3][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)=[O:10]

Participants

Conditions

Temperature: 90 °C

Procedure

Palladium (II) acetate (0.449 g, 0.002 mol) was added to a mixture of N-allyl-2,2,2-trifluoroacetamide (4.2 g, 0.02 mol), 1-bromo-3-nitrobenzene (5.09 g, 0.03 mol) and TBAA. The reaction mixture was flushed with argon and heated under argon at 90° C. for 4 h. The reaction mixture was partitioned between EtOAc and water. Organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give dark brown viscous liquid. Purification by flash chromatography (5% to 30% EtOAc—hexane gradient) gave 2,2,2-trifluoro-N-(3-(3-nitrophenyl)allyl)acetamide as light yellow solid. Yield (3.5 g, 61%); 1H NMR (400 MHz, DMSO-d6) δ 9.77 (br.s, 1H), 8.27 (s, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.93 (d, J=7.6 Hz, 1H), 7.63 (t, J=8.0 Hz, 1H), 6.71 (d, J=16.0 Hz, 1H), 6.51 (dt, J=5.6, 16.0 Hz, 1H), 4.02 (t, J=5.6 Hz, 2H).

Workup

customThe reaction mixture was flushed with argon
customThe reaction mixture was partitioned between EtOAc and water
dry with materialOrganic layer was dried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure
customto give dark brown viscous liquid
customPurification by flash chromatography (5% to 30% EtOAc—hexane gradient)

Sources & evidence

ORD record: ord-a1c467d6ddd54066a8e277b164ec001a
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674137B2

Reaction notes

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