Sodium Carbonate → HCID 22054934, compound

HRID 1829811Notes

Reaction equation

HRID 1829811 reaction equation
I[C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[S:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[Cl:9][C:10]1[S:14][C:13]([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 122723-IodophenolHCID 27343245-Chlorothiophene-2-boronic acid

Product 1

HCID 22054934HCID 22054934, compoundYield 91.9%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 3-iodophenol (1.0 g, 4.55 mmol) in DME (10 ml) was added Pd(PPh3)4 (263 mg, 0.227 mmol) at ambient temperature under N2. After stirring for 20 min., 5-chlorothiophene-2-boronic acid (886 mg, 5.45 mmol) and a solution of Na2CO3 (723 mg, 6.82 mmol) in H2O (3 ml) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and partitioned between ethyl acetate (30 ml) and H2O. The organic layer was washed with saturated NaHCO3 aqueous solution, H2O and then brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (15 g) chromatography eluting with hexane/ethyl acetate (10:1) to give 3-(5-chloro-2-thienyl)phenol (0.88 g, 91.9%).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. custompartitioned between ethyl acetate (30 ml) and H2O
  3. washThe organic layer was washed with saturated NaHCO3 aqueous solution, H2O
  4. dry with materialbrine, dried (sodium sulfate)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel (15 g) chromatography
  7. washeluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-8d6bd07a701f4f68a7f0e306d375c378
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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