HCID 24850931, compound → 5,5'-(2,5-Bis(methylsulfinyl)-1,4-phenylene)bis(2-pentylthiophene)

HRID 384237Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([S:8]([CH3:10])=[O:9])[C:5](Br)=[CH:4][C:3]=1[S:12]([CH3:14])=[O:13].CC1(C)C(C)(C)OB([C:23]2[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=2)O1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][S:12]([C:3]1[CH:4]=[C:5]([C:23]2[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=2)[C:6]([S:8]([CH3:10])=[O:9])=[CH:7][C:2]=1[C:23]1[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=1)=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

1,4-dibromo-2,5-bis(methylsulfinyl)benzene 3 (1 g, 2.8 mmol) was added to a solution of 4,4,5,5-tetramethyl-2-(5-pentylthiophen-2-yl)-1,3,2-dioxaborolane (3.4 g, 12.2 mmol) in anhydrous THF (17 mL), and the resulting mixture was purged with nitrogen for 30 min. Pd(PPh3)4 (87 mg, 0.075 mmol) was then added, and the 15 reaction mixture was heated to 60° C. overnight. The mixture was extracted with dichloromethane and washed with brine. The filtrate was dried over Mg2SO4, filtered, and the solvent removed in vacuo. The crude product was purified by flash chromatography (silica gel, eluent: hexane/EA) 3:1) to afford 0.885 g (63%) of 2a.

Workup

customthe resulting mixture was purged with nitrogen for 30 min
customthe 15 reaction mixture
extractionThe mixture was extracted with dichloromethane
washwashed with brine
dry with materialThe filtrate was dried over Mg2SO4
filtrationfiltered
customthe solvent removed in vacuo
customThe crude product was purified by flash chromatography (silica gel, eluent: hexane/EA) 3:1)

Sources & evidence

ORD record: ord-6af5f6d79bab4a829b77d42ef600d97b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367717B2

Reaction notes

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