Bromine → 1-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

HRID 1359209Notes

Reaction equation

HRID 1359209 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:27]=[CH:26][CH:25]=[CH:24][C:15]=3[C:16]=1[C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=[CH:5]2.[Br:28]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:28][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:27]=[CH:26][CH:25]=[CH:24][C:15]=3[C:16]=1[C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8]2

Participants

5

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827821-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

Product 1

HCID 181828161-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanoneYield 44.2%

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]-3,3-dimethyl-1-butanone (0.378 g, 1.05 mmol) was brominated using, bromine (0.08 mL, 1.6 mmol), and potassium acetate (1.02 g, 10.4 mmol), in glacial acetic acid (17 mL). Purification by flash chromatography (Biotage apparatus) using 15-20% chloroform in hexane as an eluant furnished the title compound as a dark brown gum (0.203 g). 1HNMR (300 MHz, DMSO-d6): δ10.95 (s, 1H), 8.35 (s, 1H), 8.2 (d, 1H, J=8.3 Hz), 8.0 (d, 1H, J=8.3 Hz), 7.95 (t, 2H, J=8.3 Hz), 7.85 (d, 1H, J=8.3 Hz), 7.35-7.55 (m, 3H), 2.65 (s, 2H), and 0.85 ppm (s, 9H).

Workup

  1. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-43caa055ebf44eccbf6b49a55084559c
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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