Boron trifluoride → HCID 10147272, compound

HRID 1004566Notes

Reaction equation

HRID 1004566 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[NH:24]1[CH:28]=[N:27][C:26]([SH:29])=[N:25]1.B(F)(F)F>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:24]2[CH:28]=[N:27][C:26]([S:29][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)=[N:25]2)([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 76379Tris(4-chlorophenyl)methanolHCID 178527894HCID 178527894, compound

Product 1

HCID 10147272HCID 10147272, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 5(b) was followed, using 1.26 g (3.47 mmol) of tris(4-chlorophenyl)methanol, 0.52 g (5.1 mmol) of 1,2,4-triazole-3-thiol, 4.0 mL of CH2Cl2 and 1.25 mL (10 mmol) of BF3 etherate. Isolation followed by flash chromatography (75 g SiO2, 40% EtOAc-hexanes) gave 0.51 g of the title compound, followed by 0.71 g of an unstable product that turned into the title compound upon standing in solution. A 0.44 g sample of the first-eluted material was recrystallized from MeOH giving 0.18 g of (15), m.p. 219°-221° C. (dec).

Sources & evidence

ORD record
ord-32bdabda974047248fa00114a03ebbbb
Source dataset
uspto-grants-2000_04
Patent number
US06051573

Reaction notes

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