Cesium carbonate → 4-{[3-Butyl-2-(4-fluorophenyl)-1-naphthalenyl]oxy}benzaldehyde

HRID 1992937Notes

Reaction equation

HRID 1992937 reaction equation
[CH2:1]([C:5]1[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:7]([OH:15])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].F[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH2:1]([C:5]1[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:7]([O:15][C:24]2[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 685361133-Butyl-2-(4-fluorophenyl)-1-naphthalenol

Product 1

HCID 860871214-{[3-Butyl-2-(4-fluorophenyl)-1-naphthalenyl]oxy}benzaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Butyl-2-(4-fluorophenyl)-1-naphthalenol (166) (0.25 g, 0.83 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMSO at 100° C. to give 0.26 g (78%) of the title compound (167) as a colorless viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.78 (t, J=7.3 Hz, 3H), 1.20-1.30 (m, 2H), 1.40-1.50 (m, 2H), 2.56 (t, J=7.9 Hz, 2H), 6.68 (d, J=8.6 Hz, 2H), 6.95 (t, J=8.7 Hz, 2H), 7.06-7.14 (m, 2H), 7.40 (t, J=7.6 Hz, 1H), 7.51 (t, J=7.2 Hz, 1H), 7.63 (d, J=8.6 Hz, 2H), 7.71 (s, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 9.81 (s, 1H). LCMS (ESI): m/z 399 (M+H)+.

Sources & evidence

ORD record
ord-d6e4fd5fa69e4fc89b1e1232deecd5bc
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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