1-(Bromomethyl)-2,3-difluoro-benzene → HCID 71117428, compound

HRID 2368538Notes

Reaction equation

HRID 2368538 reaction equation
ClC1C=CC=C(F)C=1COC1N(C2C=CC=CC=2C(F)(F)F)C(SCC2C(F)=CC=CC=2Cl)=NN=1.[Cl:36][C:37]1[CH:38]=[C:39]([N:43]2[C:47]([S:48][CH2:49][C:50]3[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][C:51]=3[Cl:57])=[N:46][N:45]=[C:44]2[OH:58])[CH:40]=[CH:41][CH:42]=1.Br[CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([F:67])[C:62]=1[F:68].C[O-].[Na+]>CN(C=O)C>[Cl:36][C:37]1[CH:38]=[C:39]([N:43]2[C:44]([O:58][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[C:63]([F:67])[C:62]=3[F:68])=[N:45][N:46]=[C:47]2[S:48][CH2:49][C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][C:51]=2[Cl:57])[CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 10942334Sodium MethoxideHCID 71491312HCID 71491312, compoundHCID 178518945HCID 178518945, compound

Product 1

HCID 71117428HCID 71117428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-chlorophenyl)-3-((2,4-dichlorobenzyl)thio)-5-((2,3-difluorobenzyl)oxy)-4H-1,2,4-triazole (599) was prepared in a similar manner as that described for the synthesis of compound 598 using 4-(3-chlorophenyl)-5-((2,4-dichlorobenzyl)thio)-4H-1,2,4-triazol-3-ol (50 mg, 0.129 mmol), 1-(bromomethyl)-2,3-difluorobenzene (40 mg, 0.194 mmol), sodium methoxide (17.4 mg, 0.322 mmol), and DMF (1.0 mL). 1H NMR (400 MHz, CDCl3) δ: 7.40-7.39 (m, 2H), 7.34-7.31 (m, 2H), 7.25-7.05 (m, 6H), 5.11 (s, 2H), 4.24 (s, 2H). LC-MS ESI m/z; found 512.0 [M+H]+.

Sources & evidence

ORD record
ord-2a12671560834e8d81d214c3ccea3a9c
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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