Iodine → HCID 178447924, compound

HRID 1608892Notes

Reaction equation

HRID 1608892 reaction equation
C([Li])CCC.[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].[I:23]I.O>CCCCCC.O1CCCC1>[CH2:6]([C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:16]=[C:17]([F:22])[C:18]([I:23])=[C:19]([F:21])[CH:20]=2)[CH2:13][CH2:14]1)[CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 178418339ButyllithiumHCID 178447923HCID 178447923, compound

Product 1

HCID 178447924HCID 178447924, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

5.9 ml of a 1.6N butyllithium solution in hexane are added dropwise during 20 min. to a solution of 2.14 g of 1-(trans-4-propylcyclohexyl)-3,5-difluorobenzene in 20 ml of dry tetrahydrofuran at -70° C. and the mixture is left to react at -70° C. for 1 hr. Then, a solution of 2.4 g of iodine in 10 ml of dry tetrahydrofuran is added dropwise within 10 min. at -60° and the mixture is gradually warmed to room temperature over a period of a further 30 min. The resulting yellow solution is thereafter treated with 10 ml of water and then with 10 ml of a 10 percent aqueous sodium bicarbonate solution and extracted with ether. The ether solution is washed with saturated sodium chloride solution and several times with water, dried over magnesium sulphate, filtered and concentrated. Chromatography of the residue over 150 g of silica gel with hexane gives 3.27 g of 1-(trans-4-propylcyclohexyl)-3,5-difluoro-4-iodobenzene as a colorless liquid.

Workup

  1. waitthe mixture is left
  2. customto react at -70° C. for 1 hr
  3. extractionwith 10 ml of a 10 percent aqueous sodium bicarbonate solution and extracted with ether
  4. washThe ether solution is 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-34857fcfdcc94419988a46846eeeb68f
Source dataset
uspto-grants-1995_03
Patent number
US05399292

Reaction notes

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