Ethanol → 2-Fluoro-3,4-dihydroxy-5-nitrobenzonitrile

HRID 2260265Notes

Reaction equation

HRID 2260265 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[C:8]([O:11]C)[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][C:3]=1[C:4]#[N:5].B(Br)(Br)Br.C(O)C>C(Cl)Cl>[F:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromide2×HCID 214591212-Fluoro-3-hydroxy-5-nitro-p-anisonitrile

Product 1

HCID 214589472-Fluoro-3,4-dihydroxy-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

550 mg of 2-fluoro-3-hydroxy-5-nitro-p-anisonitrile are dissolved in 30 ml of methylene chloride, whereupon the solution is treated with 0.44 ml of boron tribromide. After stirring at 23° for 6 hours an additional 0.1 ml of boron tribromide are added thereto, whereupon the mixture is stirred at 23° for an additional 1.5 hours. Thereupon, ml of ethanol are added thereto at -15°. The reaction mixture is evaporated and the residue is dried in a high vacuum at 23°. By recrystallization from ether/hexane there is obtained 2-fluoro-3,4-dihydroxy-5-nitrobenzonitrile of m.p. 154°.

Workup

  1. additionare added
  2. customat -15°
  3. customThe reaction mixture is evaporated
  4. customthe residue is dried in a high vacuum at 23°
  5. customBy recrystallization from ether/hexane there

Sources & evidence

ORD record
ord-860b099832c94115bea5fb96aa40acb7
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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