Sodium Carbonate → HCID 67495651, compound

HRID 450500Notes

Reaction equation

HRID 450500 reaction equation
Br[C:2]1[C:3]([O:18][CH3:19])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]1[S:5][C:4]([C:14]([O:16][CH3:17])=[O:15])=[C:3]([O:18][CH3:19])[C:2]=1[C:24]1[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 67503566HCID 67503566, compound

Product 1

HCID 67495651HCID 67495651, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.84 g of compound of step A, 4.10 g of 4-chlorophenylboronic acid and 21.68 ml of a 2M solution of sodium carbonate are added to 60 ml of toluene. Argon is bubbled through for 30 min, before adding 1.25 g of Tetrakis. Heating is carried out at 110° C. overnight. After a return to ambient temperature, 60 ml of distilled water are added and the mixture is extracted with 60 ml of ethyl acetate, and the organic phase is dried and evaporated. The product obtained is purified by silica chromatography (eluent: heptane/ethyl acetate (80/20; v/v)). 4.90 g of the expected compound are obtained.

Workup

  1. customArgon is bubbled through for 30 min
  2. additionbefore adding 1.25 g of Tetrakis
  3. temperatureHeating
  4. additionAfter a return to ambient temperature, 60 ml of distilled water are added
  5. extractionthe mixture is extracted with 60 ml of ethyl acetate
  6. customthe organic phase is dried
  7. customevaporated
  8. customThe product obtained
  9. customis purified by silica chromatography (eluent: heptane/ethyl acetate (80/20; v/v))

Sources & evidence

ORD record
ord-5265863cec4e476e83b9bb2ba570e59b
Source dataset
uspto-grants-2013_07
Patent number
US08486971B2

Reaction notes

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