Thiophene, 2,3,5-tribromo- → 3-Bromo-2,5-bis(3',4'-dimethoxyphenyl)thiophene

반응식

[Br:1]C1SC(Br)=CC=1Br.COC1C=C(B(O)O)C=CC=1OC.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:32]2[S:33][C:34]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=3)=[CH:35][CH:36]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>>[Br:1][C:36]1[CH:35]=[C:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=2)[S:33][C:32]=1[C:26]1[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=1

참가 물질

반응물 3

HCID 76592Thiophene, 2,3,5-tribromo-

HCID 27347023,4-Dimethoxyphenylboronic acid

HCID 682939712,5-Bis(3',4'-dimethoxyphenyl)thiophene

생성물 1

HCID 682940913-Bromo-2,5-bis(3',4'-dimethoxyphenyl)thiophene수율 77%

실험 절차

3-bromo-2,5-bis(3′,4′-dimethoxyphenyl)thiophene (18) was prepared by the reaction of 2,3,5-tribromothiophene (17) (321 mg, 1 mmol) and (3,4-dimethoxyphenyl)boronic acid (15) (419 mg, 2.3 mmol) according to the similar procedure for compound 16. The reaction mixture was purified by column chromatography (10%-30% EtOAc in hexanes) and afforded 18 (337 mg, 77% yield) as a yellow solid. SA-60 was also isolated (97 mg, 20% yield) from the reaction above as a dark yellow solid.