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

HRID 895188Notes

Reaction equation

HRID 895188 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:3]([OH:2])[CH:12]=[CH:11]3)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 112563072-Methoxy-6-(4-methoxyphenyl)-1-phenylnaphthalene

Product 1

HCID 101718866-(4-Hydroxy-phenyl)-1-phenyl-naphthalen-2-olYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-methoxy-6-(4-methoxyphenyl)-1-phenylnaphthalene (0.36 g, 1.06 mmol) in CH2Cl2 (25 mL) at 0° C. was slowly added boron tribromide (3.2 mL of 1 N in CH2Cl2). The mixture was allowed to warm slowly to room temperature and was stirred overnight. The resulting solution was poured into water (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, evaporation of thesolvent, and purification by silica column chromatography (25% ethyl acetate-hexanes) followed by preparative reverse-phase HPLC and drying under vacuum at 105° C. yielded 0.14 g (42%) of the title compound as a white solid: mp 142-146° C.; 1H NMR (DMSO-d6): δ 6.86 (2H, d, J=8.50 Hz), 7.26-7.42 (5H, m), 7.48-7.61 (5H, m), 7.84 (1H, d, J=8.96 Hz), 8.02 (1H, d, J=1.46 Hz), 9.52 (2H, s); MS (ESI) m/z 311 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe combined organic layers were washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate, evaporation of thesolvent, and
  4. custompurification by silica column chromatography (25% ethyl acetate-hexanes)
  5. customdrying under vacuum at 105° C.

Sources & evidence

ORD record
ord-0fb1506bdaaa4dfebe496ee31be6af72
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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