Water → 7-Hydroxynaphthalene-2-carbonitrile

HRID 890953Notes

Reaction equation

HRID 890953 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([C:17]#[N:18])=[CH:14]2)=[CH:9][CH:8]=1.O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([C:17]#[N:18])=[CH:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 109541837-Methoxy-2-naphthonitrile

Product 1

HCID 222436217-Hydroxynaphthalene-2-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of BBr3 (840 μL, 8.8 mmol) in CH2Cl2 (4 mL) is added to a solution of 7-methoxy-2-naphthonitrile (646 mg, 3.53 mmol) in CH2Cl2 (6 mL). The reaction is allowed to stir for 30 hours. Water (about 5 mL) is slowly added. The pH is adjusted to 7 with saturated Na2CO3 then the mixture is extracted with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The crude material is purified by column chromatography (step gradient of 1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl12) to give 7-hydroxy-2-naphthonitrile as a white solid (477 mg, 80%). HRMS (EI) calculated for C11H7NO: 169.0528, found 169.0527.

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialThe combined organic layers are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material is purified by column chromatography (step gradient of 1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl12)

Sources & evidence

ORD record
ord-3110adf8844640d3b675706725536cd9
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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