Boron tribromide → 6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-ol

HRID 1359249Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 181827882-(6-Methoxy-naphthalen-2-yl)-3-pentyl-benzofuran

Product 1

HCID 181827756-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-olYield 64.9%

Procedure

Following the procedure described in Step 3 of Example 1, the title compound was prepared from 2-(6-methoxy-naphthalen-2-yl)-3-pentyl-benzofuran (8.0 g, 23.3 mmol) and boron tribromide (70 mL of 1 M solution in methylene chloride, 70 mmol). Purification by chromatography on a Biotage apparatus using 4% ethyl acetate in hexane as the mobile phase afforded the title compound as a solid (5.0 g), mp 100-102° C. Mass spectrum (+APCl, [M+H]+) m/z 331. 1HNMR (300 MHz, DMSO-d6): δ9.94 (s, 1H), 8.17 (s, 1H), 7.9 (d, 1H, J=8.8 Hz), 7.84-7.75 (m, 2H), 7.65 (m, 1H), 7.58 (d, 1H, J=7.3 Hz), 7.34-7.23 (m, 2H), 7.16-7.12 (m, 2H), 2.69 (t, 2H, J=7.5 Hz), 1.71 (p, 2H, J=6.9 Hz), 1.42-1.25 (m, 4H), and 0.83 ppm (t, 3H, J=6.9 Hz). Elemental Analysis for C23H22O2.0.2H2O: Calculated: C, 82.70; H, 6.76; N, 0.00. Found: C, 82.82; H, 6.73; N, 0.09.

Workup

customPurification by chromatography on a Biotage apparatus

Sources & evidence

ORD record: ord-2c94bacb65aa48f5a0c65ba43e8cf960
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599925B2

Reaction notes

Loading…