4-Bromobenzaldehyde → 4-(4-Oxo-4-(3,4,5-trimethoxyphenyl)but-2-en-2-yl)benzaldehyde

HRID 717667Notes

Reaction equation

Br[C:2]([CH3:18])=[CH:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1)=[O:5].OCC1SC(B(O)O)=CC=1.Br[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1>>[O:5]=[C:4]([C:6]1[CH:7]=[C:8]([O:16][CH3:17])[C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[CH:3]=[C:2]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1)[CH3:18]

Participants

Reactant 3

HCID 707414-Bromobenzaldehyde

HCID 43742655-Hydroxymethylthiophene-2-boronic acid

HCID 866606143-Bromo-1-(3,4,5-trimethoxyphenyl)but-2-en-1-one

Product 1

HCID 866606154-(4-Oxo-4-(3,4,5-trimethoxyphenyl)but-2-en-2-yl)benzaldehydeYield 81%

Procedure

When the product of Step A and 4-carbaldehyde-boronic acid were substituted for 5-(hydroxymethyl)thiophen-2-ylboronic acid and 4-bromobenzaldehyde, respectively, in Example 22, Step A, the similar process afforded the title compound in 81% yield, as creamy gum. 1H-NMR (CDCl3) 10.05 (s, 1H); 7.92 (d, 2H, J=8.25 Hz); 7.68 (d, 2H, J=8.28 Hz); 7.23 (s, 2H); 7.10 (s, 1H); 3.91 (s, 9H); 2.55 (s, 3H).

Sources & evidence

ORD record: ord-6e653ab579d0478389b2e31e57c477d0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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