Isopropyl iodide → 1-Bromo-2-chloro-4-isopropoxybenzene

HRID 1764899Notes

Reaction equation

HRID 1764899 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[Cl:15].I[CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:17]([CH3:19])[CH3:18])=[CH:10][C:9]=1[Cl:15]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 227354041-Bromo-2-chloro-4-isopropoxybenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A sample of K2CO3 (52.8 mmol, 7.4 g) was added to the 4-bromo-3-chloro-phenol (24 mmol, 5 g) in anhydrous DMF (100 mL) followed by the addition of 2-iodopropane (100 mmol, 10 mL). This stirred and heated at 60° C. overnight. The reaction was cooled, extracted into EtOAc (150 mL), washed with H2) (2 L), dried over MgSO4, and concentrated in vacuo, yielding 1-bromo-2-chloro-4-isopropoxybenzene as a brown oil (4.85 g, 81%). 1H NMR (CDCl3, 300 MHz): 7.35 (1H, d, J 8.7 Hz), 6.89 (1H, d, J 2.9 Hz), 6.57 (1H, dd, J 8.8 and 2.9 Hz), 4.38 (1H, m), 1.22 (6H, d, J 6.2 Hz.)

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted into EtOAc (150 mL)
  3. washwashed with H2) (2 L)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-060b3d56ed7843edbd9e908b907f4762
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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