Hydrochloric Acid → HCID 70921801, compound

HRID 880723Notes

Reaction equation

HRID 880723 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13](N)=[CH:12][C:11]=1[F:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N([O-])=O.[Na+].[I-:30].[K+].[Cl-].[NH4+]>CN(C)C=O.O.[Cu](I)I>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([I:30])=[CH:12][C:11]=1[F:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 25517Ammonium ChlorideHCID 23668193Sodium NitriteHCID 86660317HCID 86660317, compound

Product 1

HCID 70921801HCID 70921801, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

7 ml of 6M hydrochloric acid are added to a solution of 3.20 g (9.9 mmol, 1 eq) of 1,5-bis(benzyloxy)-2-fluoro-4-aminobenzene in 40 ml of N,N-dimethylformamide, cooled to 0° C. 683 mg (9.9 mmol, 1 eq) of sodium nitrite in solution in 7 ml of water are added and the reaction medium is stirred at 0° C. for 1 hour. 1.64 g (9.9 mmol, 1 eq) of potassium iodide in solution in 8 ml of water are added, followed by 190 mg (1.0 mmol, 0.1 eq) of copper iodide, and then the reaction medium is stirred at ambient temperature overnight. The reaction medium is treated with a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and evaporated. The residue is chromatographed on silica gel, elution being carried out with 75/25 heptane/dichloromethane. 3.59 g of 1,5-bis(benzyloxy)-2-fluoro-4-iodobenzene are obtained.

Workup

  1. stirringthe reaction medium is stirred at ambient temperature overnight
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-28fa49e1a57a4d73952c40669d1d52d6
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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