4-Fluorophenol → HCID 59753961, compound

HRID 750841Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:7][N:6]=1)(=O)=O.[F:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+].COCCOCCN(CCOCCOC)CCOCCOC>CC#N>[F:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])[C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[CH:7][N:6]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 5 mL round bottom flask fitted with a stirrer bar and septum was added 2 mL CH3CN and 2-methylsulfonyl-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine from from Reference Example 3 (100 mg, 0.24 mmol). Then 4-fluorophenol (10 eq., 269 mg, 2.4 mmol), K2CO3 (2 eq., 66.3 mg, 0.48 mmol) and a drop of tris[2-(2-methoxyethoxy)-ethyl]amine were added via syringe and the mixture heated at 70° C. for 2 h. By HPLC/MS, the starting material was converted to the desired product. The product was extracted from 10 mL water with 20 mL ethyl acetate, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. Flash column chromatography on silica gel (eluted with 90/10 hexanes/ethyl acetate) afforded 2-(4-fluorophenyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine: HPLC/MS: m/e=445 (M++1); Rt=4.53 min; 1H-NMR 400 MHz (CDCl3): δ 7.02 (d, J=9 Hz, 2H), 7.20-7.40 (m, 9H), 8.80 (s, 1H).

Workup

customTo a 5 mL round bottom flask fitted with a stirrer bar

Sources & evidence

ORD record: ord-8afdae1b7b9e477bb0a34c9dfbb90332
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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