3,5-Dimethoxyphenol → 2-(4-Fluorophenyl)-4,6-dimethoxy-1-benzofuran

HRID 76822

Reaction equation

HRID 76822 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:15]>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[O:15][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=3[CH:13]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 103833,5-DimethoxyphenolHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 545908692-(4-Fluorophenyl)-4,6-dimethoxy-1-benzofuranYield 49%

Procedure

This compound was prepared using Method A from 3,5-dimethoxyphenol and 2-bromo-1-(4-fluorophenyl)ethanone: Yield 49% following procedure A.2; m.p. 142-143° C.; IR 2914, 1614, 1496, 1220, 1145, 1116, 1043 cm−1; 1H-NMR (200 MHz, δ ppm, CDCl3) 7.74 (dd, J=8.8 Hz, 5.4 Hz, 2H), 7.10 (t, J=8.7 Hz, 2H), 6.96 (s, 1H), 6.68 (s, 1H), 6.33 (d, J=1.7 Hz, 1H), 3.89 (d, J=11.3 Hz, 6H); 13C-NMR (126 MHz, δ ppm, CDCl3) 162.6 (d, J=247.7 Hz), 159.5, 156.8, 153.7, 153.0, 127.4 (d, J=3.0 Hz), 126.2 (d, J=8.0 Hz), 115.9 (d, J=22.0 Hz), 113.5, 98.7, 94.6, 88.5, 55.9, 55.8.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-fd6a10535fd3482fb99cd3a9db2a0d5d
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Linked notes

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