Cesium carbonate → 4-[2-(4-Fluoro-phenyl)-6-methoxy-3-methyl-naphthalen-1-yloxy]-benzaldehyde

HRID 1992966Notes

Reaction equation

HRID 1992966 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([CH3:18])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH3:20])[CH:14]=3)[C:9]=2[O:21][CH2:22]OC)=[CH:4][CH:3]=1.Cl.O1CCOCC1.FC1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([CH3:18])=[CH:16][C:11]3[C:10](=[CH:15][CH:14]=[C:13]([O:19][CH3:20])[CH:12]=3)[C:9]=2[O:21][C:22]2[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 204431481,4-Dioxane hydrochlorideHCID 685374682-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-methyl-naphthalene

Product 1

HCID 866166674-[2-(4-Fluoro-phenyl)-6-methoxy-3-methyl-naphthalen-1-yloxy]-benzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-methyl-naphthalene (203) (0.31 g, 0.95 mmol), 4 N HCl/Dioxane (5 mL), 4-fluorobenzaldehyde (0.132 mL, 1.23 mmol), Cs2CO3 (0.838 g, 2.57 mmol) and DMSO (3 mL) were reacted as described above to give 0.263 g (72%) of the title compound (204) as oil. 1H NMR (400 MHz, d-CDCl3): δ 2.24 (s, 3H), 3.93 (s, 3H), 6.69 (d, J=8.8 Hz, 2H), 6.92-6.97 (m, 2H), 7.07-7.15 (m, 4H), 7.59-7.68 (m, 4H), 9.80 (s, 1H).

Sources & evidence

ORD record
ord-6a9956472baa4e8fa075660337a0705d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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