Aluminum(III) Chloride → 4-Bromo-2-hydroxybenzonitrile

HRID 29232

Reaction equation

HRID 29232 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10]C)[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 223467024-Bromo-2-methoxybenzonitrile

Product 1

HCID 129669614-Bromo-2-hydroxybenzonitrileYield 95.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-bromo-2-methoxy-benzonitrile (4.60 g, 21.7 mmol) in methylene chloride (20 mL) was added aluminum chloride (14.5 g, 108 mmol). After stirring under an argon atmosphere for 10 min, more methylene chloride (30 mL) was added, and the mixture left to reflux under argon overnight. The reaction was then diluted with ethyl acetate, washed with water, brine, and dried over magnesium sulfate. The solvent was removed at reduced pressure, providing (4.09 g, 95.2%) of 4-bromo-2-hydroxy-benzonitrile as a slightly gray-colored product. 1H-NMR (CDCl3) δ 7.35 (d, J=8.4 Hz, 1H), 7.19 (d, J=1.4 Hz, 1H), 7.14 (dd, J=8.4, 1.4 Hz, 1H), 6.15 (s, 1H); TLC Rf=0.78 (50% ethyl acetate—hexane).

Workup

  1. waitthe mixture left
  2. temperatureto reflux under argon overnight
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-a47f92932a3a4b5ba0fbbe4289868a2f
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Linked notes

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