Sodium Carbonate → HCID 66663720, compound

HRID 1676869Notes

Reaction equation

HRID 1676869 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[CH:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15][C:14]=2[C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:22]1[C:16]2[S:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:18]=3[C:17]=2[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 113582-BromoanisoleHCID 2734329Dibenzothiophene-4-boronic acid

Product 1

HCID 66663720HCID 66663720, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Bromoanisole (5.61 g, 30 mmol) and 4-dibenzothiopheneboronic acid (6.84 g, 30 mmol), Pd2(PPh3)4(1.00 g, 0.8 mmol) were dissolved in 100 ml of toluene. Saturated solution of sodium carbonate (12.5 g in water) was added, and reaction mixture was heated to reflux under N2 atmosphere overnight. Then reaction mixture was cooled down to room temperature, separated organic phase and evaporated toluene. The solid residue was subjected to column chromatography on silica (eluent—hexane/ethyl acetate 4/1) providing 4-(2-methoxyphenyl)dibenzo[b,d]thiophene as 6.6 g of colorless solidified oil.

Workup

  1. customreaction mixture
  2. temperaturewas heated
  3. temperatureto reflux under N2 atmosphere overnight
  4. customThen reaction mixture
  5. customseparated organic phase
  6. customevaporated toluene

Sources & evidence

ORD record
ord-80050b5066524456a6ebdaef7e37373a
Source dataset
uspto-grants-2011_08
Patent number
US08007927B2

Reaction notes

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