Dimethylformamide → 3-(4-Chloromethylphenyl)-5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole

HRID 2407502Notes

Reaction equation

S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]1[CH:16]=[C:15]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28]O)=[CH:24][CH:23]=3)[N:18]=2)[CH:14]=[CH:13][C:12]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[Cl:3][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[N:18]=[C:17]([C:15]3[CH:14]=[CH:13][C:12]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[C:11]([F:10])[CH:16]=3)[O:21][N:20]=2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Thionyl chloride (20 mL, 0.274 mol) and N,N-dimethylformamide (2 mL) are added to a stirred solution of 4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]phenylmethanol (32 g, 0.092 mol) in dichloromethane (150 mL) at 0° C. The reaction mixture is heated at 80° C. for 1 hour and then concentrated under reduced pressure. The residue is neutralized with a saturated aqueous sodium bicarbonate solution (150 mL) to furnish a solid which is filtered and washed with n-hexane (150 mL) to give 3-(4-chloromethylphenyl)-5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole.

Workup

concentrationconcentrated under reduced pressure
customto furnish a solid which
filtrationis filtered
washwashed with n-hexane (150 mL)

Sources & evidence

ORD record: ord-173a760f076c45aa8b1d4ea5c43520e6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809539B2

Reaction notes

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