Water → 1-Iodo-4-(2-methyl-1-methylene-propyl)-benzene

HRID 1805308Notes

Reaction equation

HRID 1805308 reaction equation
[Li][C:2](C)(C)C.[I:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC>[I:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[CH2:2])[CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 962WaterHCID 197647831-(4-Iodophenyl)-2-methylpropan-1-oneHCID 178418306HCID 178418306, compound

Product 1

HCID 672301281-Iodo-4-(2-methyl-1-methylene-propyl)-benzene

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7.07 g (20 mmol) of methyltriphenylphosphonium bromide in 50 mL of dry THF at 0° C. were added t-BuLi of (14.7 ml, 1.5 M in hexane) and the solution turned brown. After 1 hour of stirring at 0° C., the crude 1-(4-Iodo-phenyl)-2-methyl-propan-1-one from the last step in 20 mL of THF were added dropwise and the solution was stirred for 14 hours at room temperature. After cooling to ca. 20° C., 52 mL of water were added and the solution was extracted with dichloromethane (3×50 mL). The organic layer was dried over MgSO4 and the solvent was removed to give the crude title compound as white solid. The product was used for the next step without further purification.

Workup

  1. stirringthe solution was stirred for 14 hours at room temperature
  2. temperatureAfter cooling to ca. 20° C.
  3. extractionthe solution was extracted with dichloromethane (3×50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-937ec9f9a9fe455694b260698e91a068
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

Loading…