Potassium Carbonate → 4-chloro-2-iodo O-crotyl phenol

HRID 2101452Notes

Reaction equation

HRID 2101452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH:17]=[CH:18][CH3:19]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH:17]=[CH:18][CH3:19])=[C:4]([I:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 6202344-Chloro-2-iodophenol

Product 1

HCID 698740424-chloro-2-iodo O-crotyl phenolYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-chloro-2-iodo phenol (5.11 mmol, 1.3 g) in DMF (40 mL) and potassium carbonate (10 mmol, 1.4 g) was added crotyl bromide (10.2 mmol, 1.6 g) and the reaction mixture was stirred at room-temperature for one hour. The reaction was quenched with H2O (100 mL) and extracted with EtOAc (2×50 mL). The EtOAc layer was collected, dried, filtered and the filtrate was evaporated to obtain 4-chloro-2-iodo O-crotyl phenol (94%, 1.5 g).

Workup

  1. customThe reaction was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. customThe EtOAc layer was collected
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a0dd52fc7e5343f3aac8039f87c64079
Source dataset
uspto-grants-2009_08
Patent number
US07572910B2

Reaction notes

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