Ammonium Chloride → 3-cyclobutylphenol

HRID 2363146Notes

Reaction equation

HRID 2363146 reaction equation
[CH:1]1([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>C(Cl)Cl>[CH:1]1([C:5]2[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 58319227HCID 58319227, compound

Product 1

HCID 179184093-cyclobutylphenolYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 1-cyclobutyl-3-methoxy-benzene (155 mg, 0.95 mmol) in CH2Cl2 (2 mL) was added dropwise 1.0M-BBr2 (1.05 mL, 1.05 mmol) at 0° C. The mixture was stirred for 1 hour at 0° C., treated with saturated ammonium chloride, and then extracted with CH2Cl2. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography to give 3-cyclobutyl-phenol (100 mg, 71%).

Workup

  1. additionwas added dropwise 1.0M-BBr2 (1.05 mL, 1.05 mmol) at 0° C
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e4862231c4844d1e8c605f08681077f5
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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