6-Bromo-2-naphthalenol → 6-Hydroxy-2-naphthonitrile

HRID 2298998Notes

Reaction equation

HRID 2298998 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[Cu][C:14]#[N:15]>CN(C=O)C.C(OCC)(=O)C>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:14]#[N:15])[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 178418546HCID 178418546, compound

Product 1

HCID 45894766-Hydroxy-2-naphthonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-bromo-2-naphthol (25.0 g, 112 mmol) and copper(I) cyanide (11 g, 123 mmol) in DMF (30 mL) was heated to 135° C., stirred for 18 hours, cooled to room temperature, diluted with ethyl acetate (50 mL), triturated with 10% sodium hydroxide, and filtered through diatomaceous earth (Celite®). The filtrate was adjusted to pH 2 and extracted with ethyl acetate. The combined extracts were concentrated, dissolved in ethanol (150 mL), triturated with water, and filtered to provide the desired product.

Workup

  1. customtriturated with 10% sodium hydroxide
  2. filtrationfiltered through diatomaceous earth (Celite®)
  3. extractionextracted with ethyl acetate
  4. concentrationThe combined extracts were concentrated
  5. dissolutiondissolved in ethanol (150 mL)
  6. customtriturated with water
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f800b90182294d7b892fd020886e59f1
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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