Cesium carbonate → HCID 64315559, compound

HRID 1887476Notes

Reaction equation

HRID 1887476 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][CH:16]=[CH2:17].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:17]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1)[CH2:16][CH:15]=[CH2:14]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 21241Homoallyl bromideHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 64315559HCID 64315559, compoundYield 6.2%

Procedure

4-Trifluoromethoxy-phenylamine (2.5 g, 14 mmol), 4-bromobut-1-ene (2.0 g, 14 mmol) and Cs2CO3 (1.4 g, 4.2 mmol) were mixed together, and the mixture was stirred at ambient temperature for 7 days. The title compound (0.2 g, 6.1%) was obtained by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=10/1). 1H NMR (300 MHz, CDCl3): δ 7.12-7.02 (m, 2H), 6.58-6.53 (m, 2H), 5.80-5.46 (m, 1H), 5.20-5.11 (m, 2H), 3.17 (t, 2H, J=6.6 Hz), 2.43-2.35 (m, 2H). LC-MS: [M+1]+ 232.2.

Sources & evidence

ORD record
ord-da860e860bb34e69921aa4367f0292a1
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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