Hydrochloric Acid → HCID 58687490, compound

HRID 2052765Notes

Reaction equation

HRID 2052765 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.C([Li])CCC.[CH2:15]([CH:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)[CH2:16][CH2:17][CH2:18][CH3:19].Cl>O1CCCC1.CCCCCC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:23]2[CH2:24][CH2:25][CH:20]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:21][CH:22]=2)=[C:4]([F:9])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5660974-PentylcyclohexanoneHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 178418339Butyllithium

Product 1

HCID 58687490HCID 58687490, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

200 g (0.665 mol) of 1-bromo-3-fluoro-4-iodobenzene were dissolved in 800 ml of tetrahydrofuran, and 440 ml (0.698 mmol) of a 15 percent solution of n-butyllithium in hexane were added dropwise at −70° C. After 30 minutes, a solution of 117 g (0.698 mol) of 4-pentylcyclohexanone in 200 ml of tetrahydrofuran was added, and the batch was left to stirr for 60 minutes, hydrolysed using water and acidified using conc. hydrochloric acid. The organic phase was separated off, washed with water and dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product was subsequently dissolved in 1.4 l of toluene and, after addition of 6 g of toluenesulfonic acid, heated on a water separator until water of reaction was no longer separated off. The solution was washed with water and evaporated, and the residue was filtered through silica gel with n-heptane, giving 124 g (58%) of 4-bromo-2-fluoro-1-(4-pentylcyclohex-1-enyl)benzene as a yellow oil.

Workup

  1. waitthe batch was left
  2. waitto stirr for 60 minutes
  3. customThe organic phase was separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe crude product was subsequently dissolved in 1.4 l of toluene
  8. additionafter addition of 6 g of toluenesulfonic acid
  9. temperatureheated on a water
  10. customseparator until water of reaction
  11. customno longer separated off
  12. washThe solution was washed with water
  13. customevaporated
  14. filtrationthe residue was filtered through silica gel with n-heptane

Sources & evidence

ORD record
ord-627fd5454af64db783efaf656a88ca92
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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