Chloroform → HCID 67973500, compound

HRID 708308

Reaction equation

HRID 708308 reaction equation
Br[C:2]1[S:3][C:4](Br)=[CH:5][C:6]=1[Br:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[C:20](=[O:23])([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl>C1COCC1.O.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.CCOC(C)=O>[Br:7][C:6]1[CH:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[S:3][C:2]=1[C:11]1[CH:16]=[CH:15][C:14]([O:23][CH3:20])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 76592Thiophene, 2,3,5-tribromo-HCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 67973500HCID 67973500, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2,3,5-Tribromothiophene (6.42 g, 20 mmol), 4-methoxyphenylboronic acid (6.38 g, 42 mmol) and sodium carbonate (8.5 g, 80 mmol) were stirred in THF/water mixture (125/50 ml) for 90 min at RT under argon flushing. Pd(PPh3)4 (693 mg, 0.6 mmol) was added. The mixture was refluxed for 16 h (TLC), cooled to RT and THF was removed by evaporation. Water was added and aqueous fractions extracted with EtOAc. The organic fractions were combined, solvent removed and the crude product purified by flash chromatography (Silica gel; hexane/chloroform/EtOAc; gradient up to 20% chloroform then 20% EtOAc) to yield 3-bromo-2,5-bis(4-methoxyphenyl)thiophene (4.9 g, 13 mmol, 65%).

Workup

  1. temperatureThe mixture was refluxed for 16 h (TLC)
  2. customTHF was removed by evaporation
  3. additionWater was added
  4. extractionaqueous fractions extracted with EtOAc
  5. customsolvent removed
  6. customthe crude product purified by flash chromatography (Silica gel

Sources & evidence

ORD record
ord-4ad2ec4d58e54e07bd01dbcc2fa5da29
Source dataset
uspto-grants-2015_11
Patent number
US09176357B2

Linked notes

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