3-Fluorobenzylic alcohol → HCID 59753910, compound

HRID 750798Notes

Reaction equation

HRID 750798 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:5][N:4]=1.[F:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][OH:29]>CCCCCC.C(OCC)(=O)C>[F:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][O:29][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 680083-Fluorobenzylic alcoholHCID 597539142-Methylthio-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

Product 1

HCID 59753910HCID 59753910, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2-Methylthio-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (from Reference Example 3) was reacted with 3-fluorobenzyl alcohol according to the procedures described in Example 1 to afford 2-(3-fluorobenzyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine as the higher Rf product.(95/5 hexane/ethyl acetate TLC. HPLC/MS: 460 (M+); Rt=4.66 min; 1H-NMR 500 MHz (CDCl3): δ 5.53 (s, 2H), 7.04 (d over m, J=9 Hz, 3H), 7.2-7.3 (m, 6H), 7.36-7.4 (m, 2H), 8.61 (s, 1H).

Sources & evidence

ORD record
ord-c72ae2461900423487029655f3846846
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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