Sodium Iodide → HCID 18971735, compound

HRID 2395385Notes

Reaction equation

HRID 2395385 reaction equation
[Si]([O:8][C:9]1[C:10]([F:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.O>[CH2:27]([O:8][C:9]1[C:10]([F:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH2:12][C:11]1[CH:15]=[CH:16][CH:17]=[CH:9][CH:10]=1)=[O:13])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 18971692HCID 18971692, compound

Product 1

HCID 18971735HCID 18971735, compoundYield 147.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-tert-butyldimethylsilyloxy-2-fluorobenzoic acid (7.74 g, 29 mmol), potassium carbonate (24.0 g, 174 mmol) and sodium iodide (25.9 g, 174 mmol) in DMF (180 ml) was added benzyl chloride (8.33 ml, 72.4 mmol) dropwise over 5 min. After stirring for 2 days the reaction mixture was poured into water (400 ml) and extracted with diethyl ether (3×200 ml). The combined extracts were washed with brine (100 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product obtained was recrystallized from 2-propanol to afford title compound (7.19 g, 74%) as white flakes.

Workup

  1. extractionextracted with diethyl ether (3×200 ml)
  2. washThe combined extracts were washed with brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product obtained
  6. customwas recrystallized from 2-propanol

Sources & evidence

ORD record
ord-3e75656805b14bf89c7e890ea8215bca
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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