Sodium Carbonate → HCID 10956973, compound

HRID 1828320Notes

Reaction equation

HRID 1828320 reaction equation
[Br:1][C:2]1[CH:6]=[C:5](Br)[S:4][C:3]=1[O:8][CH2:9][CH3:10].B(OCCCC)(OCCCC)OCCCC.I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+]>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.CCCCCC.C1COCC1>[Br:1][C:2]1[CH:6]=[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:4][C:3]=1[O:8][CH2:9][CH3:10]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 12712Tributyl borateHCID 11098115HCID 11098115, compound

Product 1

HCID 10956973HCID 10956973, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

150 ml of anhydrous THF and 6.5 g (23 mmol) of 3,5-dibromo-2-ethoxythiophene was added into a flask under argon atmosphere. Then, 15 ml (25 mmol) of a solution containing 15% n-butylithium hexane was slowly dripped into it at −78° C. After being stirred for 1 hour at −78° C., 9.1 ml (34 mmol) of tri-n-butyl borate was slowly dripped into it and was stirred for 1.5 hours. After being returned to a room temperature and quenched with water, 4.6 g (23 mmol) of iodobenzene, 1.1 g (0.95 mmol) of Pd(PPh3)4, and 50 ml of 20 wt % Na2CO3 aqueous solution was added to the solution and was refluxed overnight at 70° C. The reaction solution was extracted with ether, was washed with a salt solution, and was dried with magnesium sulfate. After filtering out the magnesium sulfate and evaporating the solvent, the product was developed with hexane on a silica column to give 3-bromo-2-ethoxy-5-phenylthiophene (Rf=0.31). The yield was 4.9 g in weight and 76% in percentage.

Workup

  1. customwas slowly dripped into it at −78° C
  2. stirringwas stirred for 1.5 hours
  3. customAfter being returned to a room temperature
  4. additionwas added to the solution
  5. temperaturewas refluxed overnight at 70° C
  6. extractionThe reaction solution was extracted with ether
  7. washwas washed with a salt solution
  8. dry with materialwas dried with magnesium sulfate
  9. filtrationAfter filtering out the magnesium sulfate
  10. customevaporating the solvent

Sources & evidence

ORD record
ord-c0bf5a45251648d2b713710835b09b67
Source dataset
uspto-grants-2006_06
Patent number
US07057054B2

Reaction notes

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