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Water → 1-Bromo-6-(4-hydroxy-phenyl)-naphthalen-2-ol

HRID 1830628
Notes
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Reaction equation

HRID 1830628 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([OH:18])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1.O>C(#N)C>[Br:26][C:14]1[C:15]2[C:10](=[CH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)=[CH:17][CH:16]=2)[CH:11]=[CH:12][C:13]=1[OH:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 114590066-(4-Hydroxyphenyl)-2-naphthol

Product 1

HCID 101496841-Bromo-6-(4-hydroxy-phenyl)-naphthalen-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(4-hydroxyphenyl)-2-naphthol (4.02 g, 17.0 mmol) in acetonitrile (150 mL) at 0° C. was added NBS (3.03 g, 17.0 mmol). The reaction was stirred at 0° C. for 3 hr and then poured into water (200 mL) and extracted with ethyl acetate (3×300 mL), The combined organic layers were washed with water, dried over sodium sulfate, filtered, evaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate hexanes) yielded 5.33 g (100%) of the title compound as a tan solid. The title compound was further purified by reverse phase HPLC to yield a white solid: mp 208–210° C.; 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.47 Hz), 7.28 (1H; d, J=8.80 Hz), 7.63 (2H, d, J=8.50 Hz), 7.85 (2H, d, J=8.84 Hz), 8.02–8.06 (2H, m), 9.60 (1H, s), 10.54 (1H, s); MS (ESI) m/z 313/315 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate (3×300 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate hexanes)

Sources & evidence

ORD record
ord-0a8ebab8e53844379121951ef1f3825c
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067524B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes