3-Bromophenol → HCID 66672888, compound

HRID 422838Notes

Reaction equation

HRID 422838 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.[CH:14]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[C:28]1=[O:37])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:29]2([OH:36])[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:27]([CH:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:28]2=[O:37])=[C:4]([OH:8])[CH:3]=1

Participants

6

Reactant 3

HCID 115633-BromophenolHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 178418918HCID 178418918, compound

Product 1

HCID 66672888HCID 66672888, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-bromophenol (11.9 g, 69.2 mmol) in dichloromethane (160.0 mL) at 0° C. was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 38.0 mL, 76.1 mmol). The solution was stirred at 0° C. for 30 min, then 1-benzhydrylindoline-2,3-dione (10.0 g, 34.6 mmol) was added. The reaction was stirred at ambient temperature for 16 h, then concentrated in vacuo to dryness. The residue obtained was dissolved in ethyl acetate (400.0 mL) and washed with saturated ammonium chloride solution (3×100.0 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to dryness. Purification by flash chromatography with 30% ethyl acetate in hexanes afforded 3-(4-bromo-2-hydroxyphenyl)-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (11.7 g, 70%) as a beige solid: 1H NMR (300 MHz, CDCl3) δ 9.09 (br s, 1H), 7.47-7.16 (m, 11H), 7.12-7.00 (m, 3H), 6.92-6.84 (m, 2H), 6.72-6.66 (m, 1H), 6.51-6.45 (m, 1H), 4.57 (br s, 1H); MS (ES+) m/z 484.2 (M+1), 486.2 (M+1).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 16 h
  2. concentrationconcentrated in vacuo to dryness
  3. customThe residue obtained
  4. washwashed with saturated ammonium chloride solution (3×100.0 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to dryness
  8. customPurification by flash chromatography with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-26a1c2fde3a741c29c940ea05f7ffbbc
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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