Cesium carbonate → HCID 86616665, compound

HRID 1992952Notes

Reaction equation

HRID 1992952 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[OH:29])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:24]([C:25]([F:27])([F:28])[F:26])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[O:29][C:31]3[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 68536227HCID 68536227, compound

Product 1

HCID 86616665HCID 86616665, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-{4-[(Phenylmethyl)oxy]phenyl}-3-(trifluoromethyl)-1-naphthalenol (186) (0.25 g, 0.64 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMSO at 100° C. for 5 h using microwave synthesizer to give 0.23 g (71%) of the title compound (187) as a light brown viscous oil. 1H NMR (400 MHz, CDCl3): δ 5.01 (s, 2H), 6.67 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H), 7.30-7.44 (m, 5H), 7.57-7.68 (m, 4H), 7.88 (d, J=8.3 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H), 8.25 (s, 1H), 9.82 (s, 1H). LCMS (ESI): m/z 521 (M+Na)+.

Sources & evidence

ORD record
ord-4725f5a5190d42f6ba6f720432c18ca2
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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