1,2-Dimethoxyethane → HCID 21183146, compound

HRID 1386885Notes

Reaction equation

HRID 1386885 reaction equation
[Cl:1][C:2]1[C:3](I)=[C:4]([S:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>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.CCOCC.O>[Cl:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([S:8][CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 21183185HCID 21183185, compound

Product 1

HCID 21183146HCID 21183146, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6.0 g (21 mmol) of 3-chloro-2-iodo(methylthio)benzene, 5.1 g (42 mmol) of phenylboronic acid, 14 g (100 mmol) of potassium carbonate, 80 mL of 1,2-dimethoxyethane, and 75 mL of water was prepared and deaerated with a stream of nitrogen. Tetrakis(triphenylphosphine)palladium(0) (730 mg, 0.63 mmol) was added and the mixture was heated at about 100° C. under nitrogen with stirring for about 20 hours. Water and ether were added and the aqueous phase was extracted with more ether. The ether phase and extract were combined, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation under reduced pressure and then in a Kugelrohr apparatus at 80° C. under 0.5 mm Hg (67 Pascals) pressure. The liquid residue was chromatographed on silica eluting with an 85:15 mixture of hexane and dichloromethane to obtain 4.3 g (87 percent of theory) of the title compound as a colorless liquid.

Workup

  1. customwas prepared
  2. extractionthe aqueous phase was extracted with more ether
  3. extractionThe ether phase and extract
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customat 80° C.
  8. customThe liquid residue was chromatographed on silica eluting with an 85:15 mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-38d2013673ff4acfad7423c72830a4ef
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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