1,2-Dimethoxyethane → 4,4''-Dimethoxy-5'-{4-[2-(phenylmethyl)benzo[b]thien-3-yl]phenyl}[1,1';3',1''-terphenyl]-2'-ol

HRID 1936888Notes

Reaction equation

[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[C:27](Br)[C:26]([OH:30])=[C:25](Br)[CH:24]=2)=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.[OH-].[Ba+2].[OH-].CO[CH2:48][CH2:49][O:50][CH3:51]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([C:25]2[CH:24]=[C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:9]4[C:10]5[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=5[S:12][C:8]=4[CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:18][CH:19]=3)[CH:28]=[C:27]([C:1]3[CH:2]=[CH:3][C:49]([O:50][CH3:51])=[CH:48][CH:8]=3)[C:26]=2[OH:30])=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Palladium (II) acetate (81 mg, 0.036 mmol) was added into a mixture of 4′-(2-benzyl-benzo[b]thiophen-3-yl)-3,5-dibromo-biphenyl-4-ol (1.0 g, 1.82 mmol), 4-methoxy-benzeneboronic acid, barium hydroxide (0.93 g, 5.46 mmol), 1,2-dimethoxyethane (10 mL), and water (10 mL). The mixture was stirred at 75° C. for 10 hours, poured into water, and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 4:1) gave 4,4″-dimethoxy-5′-{4-[2-(phenylmethyl)benzo[b]thien-3-yl]phenyl}[1,1′;3′,1″-terphenyl]-2′-ol as a yellow solid (0.45 g,): mp 80-82; MS m/e 604 (M+);

Workup

extractionextracted with ethyl ether
dry with materialThe organic extracts were dried over MgSO4
customEvaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 4:1)

Sources & evidence

ORD record: ord-4af1895377a949c69743d0ec816f1897
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391897B2

Reaction notes

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