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

HRID 716764Notes

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-3f3b5d1dc3e14b04a7199e21e322c2d9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193669B2

Reaction notes

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