Bromine → 1-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

HRID 1359208Notes

Reaction equation

HRID 1359208 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][CH:19]([CH3:21])[CH3:20])[CH:6]=[CH:5]2.[Br:27]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:27][C:10]1[CH:11]=[C:2]([OH:1])[CH:3]=[C:4]2[C:9]=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][CH:19]([CH3:21])[CH3:20])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827801-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

Product 1

HCID 181827891-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanoneYield 58.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure described in Step 4 of Example 1, 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone (0.863 g, 2.51 mmol) was brominated using bromine (0.15 mL, 2.9 mmol), and potassium acetate (2.45 g. 25.0 mmol) in glacial acetic acid (25 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant followed by chromatography on a Biotage apparatus using 15-20% chloroform in hexane as an eluant furnished 1-[2-(8-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone as an orange solid (0.623 g), mp 160-161° C. 1HNMR (200 MHz, DMSO-d6): δ10.95 (s,1H), 8.4 (s, 1H), 8.2 (d, 1H, J=8.6 Hz), 7.9-8.1 (m, 3H), 7.7-7.8 (d, 1H, J=6.8 Hz), 7.3-7.55 (m, 3H), 2.8 (d, 1H, J=6.8 Hz), 2.0-2.2 (m, 1H), and 0.75 ppm (d, 6H, J=6.3 Hz).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d4b0469dba8b48f18bcd77aab09f22d1
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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