Water → HCID 18787933, compound

HRID 1106378Notes

Reaction equation

HRID 1106378 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[I:8].[Br-].[CH2:17]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:18][CH3:19].CC(C)([O-])C.[K+].O>C1COCC1>[CH:17](=[C:12]1[CH2:13][CH2:14][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([I:8])=[C:2]([F:1])[CH:3]=2)[CH2:10][CH2:11]1)[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 80374Propyltriphenylphosphonium bromideHCID 18787925HCID 18787925, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18787933HCID 18787933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

44.95 g of 4-(3-fluoro-4-iodophenyl)cyclohexanone and 55.4 g of propyltriphenylphosphonium bromide were introduced into 250 ml of THF, and the mixture was cooled to -10° C. with stirring and under nitrogen. A solution of 15.8 g of potassium tert-butoxide in 150 ml of THF was then added dropwise at -10° C. with stirring, and the mixture was then stirred at room temperature for a further 2 hours. The yellow suspension was then cooled to 10° C., and 500 ml of water were added. The organic phase was separated off, and the aqueous phase was extracted once with 100 ml of methyl tert-butyl ether. The combined organic extracts were washed once with 100 ml of water, dried using sodium sulfate, filtered and evaporated to a residue. The residue was then purified by means of a silica-gel frit, and the eluate was evaporated to a residue, giving 4-(4-propylidenecyclohexyl)-2-fluoro-1-iodobenzene.

Workup

  1. stirringwith stirring
  2. stirringthe mixture was then stirred at room temperature for a further 2 hours
  3. temperatureThe yellow suspension was then cooled to 10° C.
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted once with 100 ml of methyl tert-butyl ether
  6. washThe combined organic extracts were washed once with 100 ml of water
  7. customdried
  8. filtrationfiltered
  9. customevaporated to a residue
  10. customThe residue was then purified by means of a silica-gel frit
  11. customthe eluate was evaporated to a residue

Sources & evidence

ORD record
ord-b8ec7dff90b74701be7dfa19b837807c
Source dataset
uspto-grants-2000_05
Patent number
US06057006

Reaction notes

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