Ethyl bromoacetate → [1-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

HRID 1359254Notes

Reaction equation

HRID 1359254 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:25]=[CH:24][CH:23]=[CH:22][C:15]=4[C:16]=3[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:26].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CC(C)=O>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][O:26][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3[O:13][C:14]4[CH:25]=[CH:24][CH:23]=[CH:22][C:15]=4[C:16]=3[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=2)[C:2]=1[Br:1])[CH3:39]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 181827781-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol

Product 1

HCID 69830702[1-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure described in Method B, Step 5 of Example 1, the title compound was prepared from 1-bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol (1.5 g, 3.66 mmol), cesium carbonate (2.4 g, 7.34 mmol), ethyl bromoacetate (0.48 mL, 4.3 mmol) in acetone (35 mL). The title compound was obtained as an off-white solid (1.6 g), mp 93-95° C. Mass spectrum (+APCl, [M+H]+) m/z 495. 1HNMR (300 MHz, DMSO-d6): δ8.34 (s, 1H), 8.24 (d, 1H, J=9.0 Hz), 8.12 (d, 1H, J=9.1 Hz), 8.06-8.02 (m, 1H), 7.69 (d, 1H, J=7.1 Hz), 7.61 (d, 1H, J=7.7 Hz), 7.48 (d, 1H, J=9.1 Hz), 7.37-7.26 (m, 2H), 5.1 (s, 2H), 4.18 (q, 2H, J=7.1 Hz), 3.01 (t, 2H, J=7.3 Hz), 1.76-1.64 (m, 2H), 1.43-1.26 (m, 4H), 1.22 (t, 3H, J=7.1 Hz), and 0.85-0.79 ppm (m, 3H). Elemental Analysis for C27H27BrO4.1.0H2O: Calculated: C, 63.16; H, 5.69; N, 0.00. Found: C, 62.90; H, 5.19; N, 0.15.

Sources & evidence

ORD record
ord-fd3a2f837a6843f3aeac22215c5387dd
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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