Sodium Carbonate → HCID 18694306, compound

HRID 1870876Notes

Reaction equation

HRID 1870876 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([OH:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:16]2[CH:17]=[CH:18][C:13]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 233594-Bromo-3-methylanilineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 18694306HCID 18694306, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromo-3-methylaniline (7.40 g, 40 mmol) and 4-carboxybenzeneboronic acid (7.90 g, 48 mmol) were stirred in 1,2-dimethyoxyethane (DME) (150 ml). Anhydrous sodium carbonate (19.0 g, 179 mmol) was dissolved in water (150 ml) and added to the above. The mixture was then purged with a stream of argon for 15 minutes. Tetrakis (triphenylphosphine)palladium (O) (0.25 g, 0.2 mmol) was added, and the mixture was stirred at reflux for 20 h under argon. DME was removed by evaporation under reduced pressure, and the clear residue was acidified with 5M HCl to yield a thick grey suspension. The solid was filtered off, washed with water and dried in vacuo at 60° C., to give the title compound (9.60 g, quantitative).

Workup

  1. additionadded to the above
  2. customThe mixture was then purged with a stream of argon for 15 minutes
  3. temperatureat reflux for 20 h under argon
  4. customDME was removed by evaporation under reduced pressure
  5. customto yield a thick grey suspension
  6. filtrationThe solid was filtered off
  7. washwashed with water
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-b2970769905e46728e47d3446f56344a
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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