Bromine → 1-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol

HRID 1359253Notes

Reaction equation

HRID 1359253 reaction equation
[CH2:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([OH:25])[CH:19]=[CH:18]2)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:26]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:26][C:21]1[C:22]2[C:17](=[CH:16][C:15]([C:7]3[O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:6]=3[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[OH:25]

Participants

5

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827756-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-ol

Product 1

HCID 181827781-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-olYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure described in Step 4 of Example 1, 6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol (3.3 g, 10.0 mmol) was brominated using bromine (0.6 mL, 11.8 mmol), and potassium acetate (1.0 g. 10.2 mmol) in glacial acetic acid (40 mL). Purification by chromatography on a Biotage apparatus using 5% % ethyl acetate in hexane as the mobile phase furnished the title compound as an off-white solid (3.6 g), mp 75-77° C. Mass spectrum (+APCl, [M+H]+) m/z 409. 1HNMR (300 MHz, DMSO-d6): δ10.76 (br s,1H), 8.25 (d, 1H, J=1.2 Hz), 8.14 (d, 1H, J=8.9 Hz), 7.98-7.92 (m, 2H), 7.68-7.58 (m, 2H), 7.35-7.27 (m, 3H), 2.98 (t, 2H, J=7.3 Hz), 1.71 (p, 2H, J=6.9 Hz), 1.42-1.27 (m, 4H), and 0.87-0.80 ppm (tm 3H). Elemental Analysis for C23H21BrO2.0.7H2O: Calculated: C, 65.47; H, 5.35; N, 0.00. Found: C, 65.17; H, 4.92; N, 0.08.

Workup

  1. customPurification by chromatography on a Biotage apparatus

Sources & evidence

ORD record
ord-f6a9e8e9dad44b5bbc4f3e41c2836aea
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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