Iodine → HCID 178447924, compound

HRID 1492104Notes

Reaction equation

HRID 1492104 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 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

5.9 ml of a 1.6N butyllithium solution in hexane were 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 detrahydrofuran at -70° C. and the mixture was left to react at -70° C. for 1 hr. Then, a solution of 2.4 g of iodine in 10 ml of dry tetrahydrofuran was added dropwise at -60° C. within 10 min. and the mixture was gradually warmed to room temperature during a further 30 min. The yellow solution obtained was treated with 10 ml of water and then with 10 ml of a 10 percent aqueous sodium bicarbonate solution extracted with ether. The ether solution was washed with sat. 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 gave 3.27 g of 1-(trans-4-propylcyclohexyl)-3,5-difluoro-4-iodobenzene as a colourless liquid.

Workup

  1. waitthe mixture was left
  2. customto react at -70° C. for 1 hr
  3. customThe yellow solution obtained
  4. extractionwith 10 ml of a 10 percent aqueous sodium bicarbonate solution extracted with ether
  5. washThe ether solution was washed with sat. sodium chloride solution and several times with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aebf6e7333274123bfa08aae1d524660
Source dataset
uspto-grants-1994_12
Patent number
US05372746

Reaction notes

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