Bromine → 1-Bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol

HRID 1359215Notes

Reaction equation

HRID 1359215 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:28]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:28][C:23]1[C:24]2[C:19](=[CH:18][C:17]([C:9]3[O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:8]=3[CH2:7][CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:26][CH:25]=2)[CH:20]=[CH:21][C:22]=1[OH:27]

Participants

5

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827796-[3-(2-Cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol

Product 1

HCID 181828001-Bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphtholYield 74.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure described in Step 4 of Example 1, 6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol (0.671 g, 1.88 mmol) was brominated with bromine (0.11 mL, 2.2 mmol) and potassium acetate (1.91 g, 19.5 mmol) in glacial acetic acid (19 mL). Purification by flash chromatography using 100% hexane and 1-30% chloroform in hexane as eluants afforded 1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol as a light brown semi-solid (0.609 g). 1HNMR (300 MHz, DMSO-d6): δ10.75 (s, 1H), 8.25 (s, 1H), 8.15 (d, 1H, J=8.6 Hz), 7.95-8.0 (m, 2H), 7.7 (d, 1H, J=8.6 Hz), 7.6 (d, 1H, J=8.6 Hz), 7.25-7.4 (m, 3H), 3.0 (t, 2H, J=8.6 Hz), 1.65-1.95 (m, 5H), 1.4-1.65 (m, 4H), and 1.1-1.25 ppm (m, 2H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-778846802daa412a8a0b782b075b84fe
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…