Water → 1-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

HRID 1359193Notes

Reaction equation

HRID 1359193 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:5]2.C([O-])(=O)C.[K+].[Br:32]Br.O>C(O)(=O)C>[Br:32][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517044Potassium AcetateHCID 113368791-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

Product 1

HCID 113846851-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanoneYield 94.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To an ice-cooled mixture of 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.59 g, 4.62 mmol) in glacial acetic acid (50 mL) was added potassium acetate (4.54 g, 46.2 mmol). The mixture was stirred at room temperature for 15 minutes and then chilled again in an ice bath. Bromine (0.27 mL, 5.3 mmol) in acetic acid (6 mL) was added dropwise. The mixture was stirred at room temperature for 15 minutes. It was poured into excess water and filtered. The precipitate was dissolved in ethyl acetate, with some warming, and dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to dryness to afford 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone as a yellow solid (1.85 g), mp 171-172° C. Mass spectrum (+APCl, [M+H]+) m/z 423. 1HNMR (400 MHz, DMSO-d6): δ10.95 (s, 1H), 8.4 (d, 1H, J=1.7 Hz), 8.15 (d, 1H, J=9.0 Hz), 8.05-8.1 (m, 2H), 7.95 (dd, 1H, J=8.8 Hz and 2.0 Hz), 7.7-7.75 (m, 1H), 7.35-7.45 (m, 3H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C23H19BrO3. 0.25 H2O: Calculated: C, 64.57; H, 4.59; N, 0.00. Found: C, 64.19; H, 4.26; N, 0.05.

Workup

  1. temperaturechilled again in an ice bath
  2. stirringThe mixture was stirred at room temperature for 15 minutes
  3. filtrationfiltered
  4. dissolutionThe precipitate was dissolved in ethyl acetate, with some warming
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-649c7ac4388c42689c771ec990d65a35
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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