Sodium Carbonate → HCID 66607868, compound

HRID 221064Notes

Reaction equation

HRID 221064 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH2:8][C:9]2[S:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[CH:7]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(COC)OC.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([CH2:8][C:9]2[S:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 66608266HCID 66608266, compound

Product 1

HCID 66607868HCID 66607868, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the above 5-bromo-1-(5-chloro-2-thienylmethyl)-2-iodobenzene (1.0 g) in dimethoxyethane (10 ml) were added phenylboronic acid (310 mg), bis(triphenylphosphine)palladium (II) dichloride (85 mg) and 2M aqueous sodium carbonate solution (3.8 ml), and the mixture was stirred at 50° C. overnight. Added thereto was a saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give 5-bromo-1-(5-chloro-2-thienylmethyl)-2-phenylbenzene (683 mg) as oil.

Workup

  1. additionAdded
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-4467ed2c8e304babb8aff267eeabe48f
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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