Water → 4-Iodo-2-isobutylphenol

HRID 971370Notes

Reaction equation

HRID 971370 reaction equation
B(Br)(Br)Br.[I:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:7]=1.O.C(Cl)Cl.CO>C(Cl)Cl>[I:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 12134704HCID 12134704, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 225652554-Iodo-2-isobutylphenolYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2.43 ml (2.43 mmol, 2.98 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 176.0 mg (0.61 mmol) 4-Iodo-2-isobutylanisole in 25 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 3 h at 0° C. and then for 12 h at r.t. The reaction mixture was then added to water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (3+1)) yielded 84.5 mg (0.31 mmol, 50.17%) 4-Iodo-2-isobutylphenol as a colorless oil.

Workup

  1. waitfor 12 h at r.t
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-87eaebc69d4d40ef972e47c023d7e3d7
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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