Sodium Carbonate → HCID 22274686, compound

HRID 494854Notes

Reaction equation

HRID 494854 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[I:17]N1C(=O)CCC1=O.[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+].P([O-])(O)(O)=O.[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[CH:5]=[C:6]([I:17])[C:7]=1[OH:8]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 516951Monobasic potassium phosphateHCID 222745023'-Fluoro-4'-hydroxy[1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 22274686HCID 22274686, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3′-Fluoro-4′-hydroxy-1,1′-biphenyl-4-carbonitrile (320 mg, 1.50 mmol) was dissolved into DMF (7 mL) and treated with N-iodosuccinimide (360 mg, 1.60 mmol). The solution was stirred at room temperature overnight. Then the mixture was poured into an aqueous mixture of Na2SO3 and Na2CO3, adjusted to pH 9 with aqueous potassium dihydrogen phosphate, and extracted with ether. The combined organic phases were dried (Na2SO4) and concentrated to provide the title compound as a pinkish solid (100% yield). MS (ESI APCI negative ion detection) m/z 338 (M−H)−.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-934bc1bd09b7454e9eac16d552ef3692
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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