Sodium Carbonate → HCID 15872362, compound

HRID 1456294Notes

Reaction equation

HRID 1456294 reaction equation
I[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=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>[CH3:26][O:27][C:28]1[CH:33]=[C:32]([C:2]2[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[C:3]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 15337859HCID 15337859, compound

Product 1

HCID 15872362HCID 15872362, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-iodo-3-(4-benzyloxyphenoxy)benzo[b]thiophene (5.00 g, 11.0 mmol) in 50 mL of toluene under N2 were added 3-methoxyphenylboronic acid (2.00 g, 13.0 mmol), (Ph3P)4Pd (0.75 g, 0.66 mmol), and 18.0 mL of 2.0N Na2CO3 solution. The resulting mixture was heated to reflux for 2 h. Upon cooling to room temperature, the reaction was diluted with EtOAc and extracted several times with 0.1N NaOH. The organic was then dried (Na2SO4) and concentrated in vacuo to an oil. Chromatography (SiO2, 0-10% Et2O/hexanes) provided 4.8 g (99%) of 2-(3-methoxyphenyl)-3-(4-benzyloxyphenoxy)benzo[b]thiophene as a brown oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. extractionextracted several times with 0.1N NaOH
  4. dry with materialThe organic was then dried (Na2SO4)
  5. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-18798c801b6c41098099bf39323ee1d9
Source dataset
uspto-grants-1998_12
Patent number
US05843965

Reaction notes

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