Hexane → HCID 59489062, compound

HRID 607487Notes

Reaction equation

HRID 607487 reaction equation
[CH2:1]([C:4]1[S:8][C:7]([C:9]2[S:10][C:11]([C:14]3[S:15][C:16](Br)=[CH:17][CH:18]=3)=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].B([O-])([O-])O[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].CCCCCC>C(COC)OC.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.O>[CH2:1]([C:4]1[S:8][C:7]([C:9]2[S:10][C:11]([C:14]3[S:15][C:16]([C:22]4[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=4)=[CH:17][CH:18]=3)=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 59489063HCID 59489063, compoundHCID 86645551HCID 86645551, compound

Product 1

HCID 59489062HCID 59489062, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-propyl-5″-bromo-2,2′:5′,2″-terthiophene (2) (0.51 g; 1.38 mmol), 4-pentylphenyl borate (50.48 g; 1.85 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.037 g; 0.03 mmol) were dissolved in dimethoxyethane (50 ml) and a 10 wt % sodium carbonate aqueous solution (50 ml) was added thereto, followed by reflux for 1 hour. After cooling to room temperature, a precipitate generated as a result of addition of water was separated by filtration, followed by purification with silica gel column chromatography (developing solvent: cyclohexane). Then, the resultant was recrystallized with n-hexane (yield: 0.47 g (1.08 mmol; yield percentage: 78%)).

Workup

  1. temperatureby reflux for 1 hour
  2. customwas separated by filtration
  3. customfollowed by purification with silica gel column chromatography (developing solvent: cyclohexane)

Sources & evidence

ORD record
ord-0cd5c3855e24411aa4896b10dd20ae1a
Source dataset
uspto-grants-2011_03
Patent number
US07915609B2

Reaction notes

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