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

HRID 1773967Notes

Reaction equation

HRID 1773967 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:17]([CH3:19])[CH3:18]>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([O:8][CH:17]([CH3:19])[CH3:18])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 8203925-Bromo-2-chlorophenol

Product 1

HCID 210710294-Bromo-1-chloro-2-isopropoxybenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-bromo-2-chlorophenol (2.08 g, 10 mmol, 1.0 eq.) and potassium carbonate (4.15 g, 30 mmol, 3.0 eq.) in MeCN (19 mL), 2-iodopropane (1.53 mL, 15 mmol, 1.5 eq.) was added. The mixture was stirred at r.t. for 18 hours. The mixture was heated up to 50° C. and stirred at that temperature for 2.5 hours. The reaction mixture was partitioned between AcOEt and water. The layers were separated and the aq. phase was extracted with AcOEt (2×). The comb. org. extracts were washed with water and sat. aq. NaCl soln., dried over MgSO4, filtered, and concentrated in vacuo to give 4-bromo-1-chloro-2-isopropoxy-benzene as a yellow oil. The product was used without further purification. LC-MS 3: tR=0.98 min; [M+H]+=no ionization

Workup

  1. temperatureThe mixture was heated up to 50° C.
  2. stirringstirred at that temperature for 2.5 hours
  3. customThe reaction mixture was partitioned between AcOEt and water
  4. customThe layers were separated
  5. extractionthe aq. phase was extracted with AcOEt (2×)
  6. washextracts were washed with water and sat. aq. NaCl soln
  7. dry with material, dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e69864f860524626bfe13b2e8becf1ae
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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