3,5-Dimethoxyphenol → 3-(4-Fluorophenyl)benzofuran-4,6-diol

HRID 76836Notes

Reaction equation

HRID 76836 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.BrC[C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=O>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[C:6]3=[C:5]([OH:11])[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]3[O:9][CH:10]=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 545910473-(4-Fluorophenyl)benzofuran-4,6-diolYield 27%

Procedure

This compound was prepared using Method B from 3,5-dimethoxyphenol and 2-bromo-1-(4-fluorophenyl)ethanone: Yield 27% following procedures B.2, B.3 and B.5; m.p. 125° C. (dec.); IR 3508, 1612, 1508, 1455, 1240, 1121, 1090, 1048 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.84 (s, 1H), 9.36 (s, 1H), 7.77 (s, 1H), 7.70 (dd, J=8.1 Hz, 5.9 Hz, 2H), 7.20 (t, J=8.8 Hz, 2H), 6.41 (s, 1H), 6.25 (s, 1H); 13C NMR (126 MHz, δ ppm, CD3OD) 163.7 (d, J=243.9 Hz), 160.2, 157.7, 153.6, 140.4, 132.0 (d, J=7.9 Hz), 130.4 (d, J=3.3 Hz), 123.3, 115.6 (d, J=21.6 Hz), 109.2, 99.1, 91.0.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-d108a25a9de148a5bc5debc1a6f09704
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Reaction notes

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