4-(Bromomethyl)-2-chloro-1-methoxybenzene → 2-[(3-Chloro-4-methoxybenzyl)thio]-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole

HRID 452700Notes

Reaction equation

HRID 452700 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([SH:15])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:20]Br>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:20][S:15][C:13]1[O:14][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)=[N:11][N:12]=1

Participants

3

Reactant 2

HCID 114703704-(Bromomethyl)-2-chloro-1-methoxybenzeneHCID 178527934HCID 178527934, compound

Product 1

HCID 445903772-[(3-Chloro-4-methoxybenzyl)thio]-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazoleYield 87%

Procedure

In the same manner as in Example 1 and using 5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole-2-thiol instead of 5-(benzothiazol-6-yl)-1,3,4-oxadiazole-2-thiol and 3-chloro-4-methoxybenzyl bromide instead of 3-(trifluoromethyl)benzyl chloride, the title compound (yield 87%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-b8245d12acb34775b344ed46383486bd
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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