1-Naphthol → 4-bromonaphthalen-1-ol

HRID 1644214Notes

Reaction equation

HRID 1644214 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:11])[CH:6]=1.[Br:12]N1C(=O)CCC1=O>CC#N>[Br:12][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]([OH:11])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 70051-NaphtholHCID 67184N-bromobutanimide

Product 1

HCID 5756094-bromonaphthalen-1-olYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of naphthol (12, 5.0 g, 35 mmol) in CH3CN (125 mL) at 0° C. was added N-bromosuccinimide (7.9 g, 45 mmole) in several portions. The reaction mixture was warmed to room temperature, stirred for 1 h, and concentrated. The residue was dissolved in EtOAc (500 mL) and the solution was washed with water (300 mL) and brine (300 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 4:1 hexanes/EtOAc) to afford 4-bromonaphthol (13, 5.0 g, 64%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.22-8.16 (m, 2H), 7.62-7.26 (m, 3H), 6.71 (d, J=8.0 Hz, 1H), 5.46 (s, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc (500 mL)
  3. washthe solution was washed with water (300 mL) and brine (300 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, 4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-3e50b182f21b4a688e5b4c737faa7dc3
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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