4-Fluoro-2-methoxybenzonitrile → 4-Fluoro-2-hydroxybenzonitrile

HRID 1372267

Reaction equation

HRID 1372267 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10]C)[CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1

Participants

4

Reactant 2

HCID 27833294-Fluoro-2-methoxybenzonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 110299014-Fluoro-2-hydroxybenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130° C. for 18 hrs. After cooling, ice water (˜50 mL) was added and the resulting mixture extracted with ether (20 mL×2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74–6.84 (2H, m, Ar—Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar—H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35. HRMS (ESI−) calcd for C7H3NOF (M−H) 136.0199. found 136.0199.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture extracted with ether (20 mL×2)
  3. washThe combined extracts were washed sequentially with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbf809677b4549c3b1fb47ef5bcff921
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Linked notes

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