Sodium Carbonate → 3-Bromo-2-methyl-5-(4-hydroxythienyl)thiophene

HRID 2068445Notes

Reaction equation

HRID 2068445 reaction equation
[Br:1][C:2]1[CH:6]=[C:5](B(O)O)[S:4][C:3]=1[CH3:10].Br[C:12]1[S:16][C:15](O)=[CH:14][CH:13]=1.C([O-])([O-])=[O:19].[Na+].[Na+]>O1CCCC1.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>[Br:1][C:2]1[CH:6]=[C:5]([C:12]2[S:16][CH:15]=[C:14]([OH:19])[CH:13]=2)[S:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12184011(4-Bromo-5-methylthiophen-2-yl)boronic acidHCID 211086275-Bromothiophene-2-ol

Product 1

HCID 673094033-Bromo-2-methyl-5-(4-hydroxythienyl)thiophene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Compound 3 is mixed with 5-bromothiophen-2-ol in the presence of tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)-4] and Na2CO3 in tetrahydrofuran (THF) for 24 h at 80° C. The crude product is distillated in vacuo and purified by silica-gel column chromatography (eluent: hexane). Compound 5 (5.01 g) is obtained as a yellowish solid.

Workup

  1. custompurified by silica-gel column chromatography (eluent: hexane)

Sources & evidence

ORD record
ord-b43a2caefdbf4968b620c2b47b276cd5
Source dataset
uspto-grants-2012_10
Patent number
US08298453B2

Reaction notes

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