Cesium carbonate → HCID 86087146, compound

HRID 1992949Notes

Reaction equation

HRID 1992949 reaction equation
[C:1]1([C:7]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[OH:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[C:1]1([C:7]2[C:16]([C:17]([F:19])([F:20])[F:18])=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[O:21][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 57295838HCID 57295838, compound

Product 1

HCID 86087146HCID 86087146, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Phenyl-3-(trifluoromethyl)-1-naphthalenol (182) (0.19 g, 0.66 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMSO at 100° C. to give 92 mg (36%) of the title compound (183) as alight brown solid. 1H NMR (400 MHz, CDCl3): δ 6.67 (d, J=8.8 Hz, 2H), 7.14 (d, J=6.9 Hz, 2H), 7.18-7.27 (m, 3H), 7.58-7.70 (m, 4H), 7.89 (d, J=8.2 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.27 (s, 1H), 9.82 (s, 1H). LCMS (ESI): m/z 415 (M+Na)+.

Sources & evidence

ORD record
ord-83765576b2cf41a89cbe822be766e780
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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