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

HRID 1992968Notes

Reaction equation

HRID 1992968 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH2:14]OC)=[C:8]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:7]([CH3:27])=[CH:6]2.Cl.O1CCOCC1.FC1[CH:43]=[CH:42][C:39]([CH:40]=[O:41])=[CH:38][CH:37]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:43]=[CH:42][C:39]([CH:40]=[O:41])=[CH:38][CH:37]=1)=[C:8]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:7]([CH3:27])=[CH:6]2

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 204431481,4-Dioxane hydrochlorideHCID 685374636-Methoxy-1-methoxymethoxy-3-methyl-2-(3-trifluoromethyl-phenyl)-naphthalene

Product 1

HCID 866166684-[6-Methoxy-3-methyl-2-(3-trifluoromethyl-phenyl)-naphthalen-1-yloxy]-benzaldehydeYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methoxy-1-methoxymethoxy-3-methyl-2-(3-trifluoromethyl-phenyl)-naphthalene (208) (0.35 g, 0.93 mmol), 4 N HCl/Dioxane (5 mL), 4-fluorobenzaldehyde (0.11 mL, 1.02 mmol), Cs2CO3 (0.364 g, 1.12 mmol) and DMF (3 mL) were reacted as described above to give 0.140 g (35%) of the title compound (209) as oil. 1H NMR (400 MHz, d-CDCl3): δ 2.26 (s, 3H), 3.95 (s, 3H), 6.68 (d, J=8.8 Hz, 2H), 7.09 (dd, J1=2.6 Hz, J2=9.2 Hz, 1H), 7.17-7.17 (m, 1H), 7.31-7.39 (m, 2H), 7.44 (s, 1H), 7.48-7.50 (m, 1H), 7.61-7.64 (m, 3H), 7.73 (d, J=9.1 Hz, 1H), 9.80 (s, 1H).

Sources & evidence

ORD record
ord-f79e264ebf374536a4d39687e55a33df
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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