Iodine → HCID 18979647, compound

HRID 1080562Notes

Reaction equation

HRID 1080562 reaction equation
C([Li])CCC.[CH2:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[CH2:7][CH3:8].[I:17]I.C(=O)(O)[O-].[Na+]>CCCCCC.O1CCCC1>[CH2:6]([C:9]1[CH:10]=[C:11]([F:16])[C:12]([I:17])=[C:13]([F:15])[CH:14]=1)[CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 807IodineHCID 516892Sodium BicarbonateHCID 189796611,3-Difluoro-5-propylbenzeneHCID 178418339Butyllithium

Product 1

HCID 18979647HCID 18979647, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

22 ml of a 1.6N butyllithium solution in hexane were added dropwise during 30 min. to a solution of 5 g of 1-propyl-3,5-difluorobenzene in 50 ml of dry tetrahydrofuran at -70° C. and left to react at -70° C. for 1 hour. Then, a solution of 8.95 g of iodine in 20 ml of dry tetrahydrofuran was added dropwise at -60° within 10 minutes and the mixture was gradually warmed to room temperature within a further 30 minutes. The resulting yellow solution was then treated with 40 ml of a 10 percent aqueous sodium bicarbonate solution and extracted with ether. The ether solution was washed with saturated sodium chloride solution and several times with water, dried over magnesium sulphate, filtered and concentrated. Chromatography of the residue over 200 g of silica gel with hexane gave 1-propyl-3,5-difluoro-4-iodobenzene as a colourless liquid.

Workup

  1. waitleft
  2. customto react at -70° C. for 1 hour
  3. extractionextracted with ether
  4. washThe ether solution was washed with saturated sodium chloride solution and several times with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c49e50a67cdc4273a899439b5ad1e423
Source dataset
uspto-grants-1996_12
Patent number
US05582767

Reaction notes

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