Sodium Carbonate → HCID 57753211, compound

HRID 225727Notes

Reaction equation

HRID 225727 reaction equation
I[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3]([C:4]([OH:6])=[O:5])=[CH:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 574452812-Iodo-5-methanesulfonyl-benzoic acid

Product 1

HCID 57753211HCID 57753211, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 6.1 mmol 2-Iodo-5-methanesulfonyl-benzoic acid (example B19(b)), 12.2 mmol 4-fluorobenzeneboronic acid, 18.4 mmol sodium carbonate and 0.3 mmol palladium (II) acetate in 30 ml water was stirred at room temperature for 48 hours. The mixture was filtered and the filtrate was acidified with HCl 37%. The mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with water and dried to provide the title compound (92%). Yellow solid. MS (m/e): 293.2 ([M−H], 100%).

Workup

  1. filtrationThe mixture was filtered
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fbfd1b2c52b44e5eaec7b98bd85bdb51
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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