Methanol → HCID 18182783, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=4)[CH:11]=3)=[C:7]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C:6]=2[CH:28]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=4)[CH:11]=3)=[C:7]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C:6]=2[CH:28]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the procedure described in Step 3 of Example 1,1-[5-chloro-2-(6-hydroxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-one was prepared 1-[5-chloro-2-(6-methoxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-one (5.6 g, 14.25 mmol), and boron tribromide (1M solution, 45 mL, 45 mmol) in methylene chloride (200 mL). After work-up, stirring of the solid residue with methanol and filtering afforded the title compound as a solid. (3.2 g), A sample was dissolved in chloroform and filtered through a plug of celite. The solvent was evaporated and the residue was crystallized from methanol to give white crystals, mp 156-157° C. Mass spectrum (+APCl, [M+H]+) m/z 379. 1HNMR (400 MHz, DMSO-d6): δ10.15 (br s,1H), 8.29 (d, 1H, J=1.2 Hz), 8.01 (d, 1H, J=2.2 Hz), 7.93 (d, 1H, J=8.8 Hz), 7.86 (d, 1H, J=8.6 Hz), 7.77-7.72 (m, 2H), 7.46 (dd, 1H, J=8.8, 2.2 Hz), 7.22 (d, 1H, J=2.2 Hz), 7.18 (dd, 1H, J=8.8, 2.4 Hz), 2.69 (t, 2H, J=7.3 Hz), 1.55-1.47 (m, 2H), 1.15-1.05 (m, 2H), and 0.68 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C23H19ClO3: Calculated: C, 72.92; H, 5.05; N, 0.00. Found: C, 72.73; H, 4.99; N, 0.08.
Workup
- filtrationfiltering
Sources & evidence
- ORD record
- ord-08ec6f8f28ff415ba99ef32bfa1884c1
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06599925B2
Reaction notes
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