Boron tribromide → 5-Hydroxynaphthalene-1-carbonitrile

HRID 2060861Notes

Reaction equation

HRID 2060861 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]#[N:14].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]#[N:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13491715HCID 13491715, compound

Product 1

HCID 158861205-Hydroxynaphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-methoxynaphthalene-1-carbonitrile (Preparation 11) (880 mg, 4.80 mmol) in DCM (10 mL) under argon at 0° C. was added 1M BBr3 solution in DCM (12.5 mL). After 10 min the mixture was maintained at rt for 4 h. The mixture was partitioned between NaHCO3 solution and EtOAc, the organic phase was washed with 1M HCl, brine and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (isohexane:EtOAc, 2:1) to give the title compound: δH (CD3OD): 6.97 (1H, d), 7.50, 7.52 (2H, 2dd), 7.62 (1H, d), 7.94 (1H, d), 8.53 (1H, d).

Workup

  1. customThe mixture was partitioned between NaHCO3 solution and EtOAc
  2. washthe organic phase was washed with 1M HCl, brine
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed in vacuo
  5. customthe residue purified by column chromatography (isohexane:EtOAc, 2:1)

Sources & evidence

ORD record
ord-6f69cdcff5914f00bfc8d38dd7609cee
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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