Acetic Acid → 5-(Bromoacetyl)-2,3-dihydroxybenzonitrile

HRID 2254825Notes

Reaction equation

HRID 2254825 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([O:15]C)[C:8]([O:13]C)=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].B(Br)(Br)Br.C(=O)([O-])O.[Na+].C(O)(=O)C>C(Cl)Cl>[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 214589615-(Bromoacetyl)-2,3-dimethoxybenzonitrile

Product 1

HCID 214590655-(Bromoacetyl)-2,3-dihydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 g of 5-(bromoacetyl)-2,3-dimethoxybenzonitrile dissolved in 150 ml of methylene chloride are treated with 8.9 ml of boron tribromide. The reaction mixture is stirred at 20° for 18 hours. It is subsequently poured into 220 ml of saturated sodium hydrogen carbonate solution and 100 g of ice, adjusted to pH 6 with glacial acetic acid and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and evaporated. There is obtained 5-(bromoacetyl)-2,3-dihydroxybenzonitrile as an amorphous solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c9befa17d5d0405caba7c12809e6f70a
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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