Ethyl Acetate → 5-Hydroxy-2-nitrobenzonitrile

HRID 2399874Notes

Reaction equation

HRID 2399874 reaction equation
C1([C:7]2[CH:8]=[C:9](OC)[C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH:14]=2)[C:12]#[N:13])C=CC=CC=1.B(Br)(Br)Br.C(OCC)(=[O:26])C>ClCCl>[C:12]([C:11]1[CH:14]=[C:7]([OH:26])[CH:8]=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])#[N:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 67809833HCID 67809833, compound

Product 1

HCID 109295425-Hydroxy-2-nitrobenzonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 578 mg (2.28 mmol) 5-phenyl-methoxy-2-nitrobenzonitrile, prepared according to the procedure of E. Elslager, et. al., J. Heterocyclic Chem. 1972, 9, 759-773, in 5 mL of dichloromethane at 0° C. was added 2.6 mL (2.62 mmol, 1.15 equiv) of a 1.0 M solution of boron tribromide in dichloromethane. After the reaction mixture was stirred for 3 h, it was diluted with ethyl acetate, washed sequentially with 1N aqueous sodium hydrogen sulfate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to give 357 mg (96%) of the title compound which was used without further purification: 1H NMR (400 MHz, CD3OD) δ8.17 (d, 1H, J=9.2 Hz), 7.03 (d, 1H, J=2.7 Hz), 6.92 (dd, 1H, J=2.7, 9.3 Hz).

Workup

  1. washwashed sequentially with 1N aqueous sodium hydrogen sulfate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-607047f2c2da438eb14bbe49befb0ea7
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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